[ CAS No. 868656-97-7 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 868656-97-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 868656-97-7 ]

SDS Specification

Alternatived Products of [ 868656-97-7 ]

Product Details of [ 868656-97-7 ]

CAS No. :	868656-97-7	MDL No. :	MFCD09836005
Formula :	C₁₀H₈BrNO₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	SKZJYJMYLUQJPG-UHFFFAOYSA-N
M.W :	254.08	Pubchem ID :	11499811
Synonyms :

Calculated chemistry of [ 868656-97-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.1
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	57.28
TPSA :	42.09 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.22
Log Po/w (XLOGP3) :	2.59
Log Po/w (WLOGP) :	2.72
Log Po/w (MLOGP) :	2.08
Log Po/w (SILICOS-IT) :	3.02
Consensus Log Po/w :	2.53

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.39
Solubility :	0.103 mg/ml ; 0.000407 mol/l
Class :	Soluble
Log S (Ali) :	-3.12
Solubility :	0.192 mg/ml ; 0.000754 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.22
Solubility :	0.0155 mg/ml ; 0.0000608 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.64

Safety of [ 868656-97-7 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280	UN#:
Hazard Statements:	H302-H317	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 868656-97-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 868656-97-7 ]
Downstream synthetic route of [ 868656-97-7 ]

[ 868656-97-7 ] Synthesis Path-Upstream 1~7

1
[ 67-56-1 ]
[ 101774-27-0 ]
[ 18107-18-1 ]
[ 868656-97-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 20℃; for 0.0333333 h;	Preparation 39 6-Bromo-lH-indole-3-carboxylic acid methyl esterTo a solution of 6-bromoindole-3-carboxylic acid (960 mg, 4.00 mmol) in methanol (9.5 mL) is added (trimethylsilyl)diazomethane (2.0 M solution in hexanes, approximately 9 mL) over two minutes at room temperature. The yellow mixture is concentrated under reduced pressure. The residue is redissolved in methanol and concentrated under reduced pressure several times to give the title compound as a solid (100percent). ES/MS m/e 256.0 (M+2).

Reference： [1] Patent: WO2007/140183, 2007, A1, . Location in patent: Page/Page column 36

2
[ 67-56-1 ]
[ 17826-04-9 ]
[ 868656-97-7 ]

Yield	Reaction Conditions	Operation in experiment
51%	Stage #1: at 20℃; for 0.0833333 h; Stage #2: at 20℃; Inert atmosphere	13b) Methyl -bromo-lH-indole-S-carboxylateTo a stirred solution of -bromo-lH-indole-S-carbaldehyde (1.6 g, 7.1 mmol) in methanol (70 mL) was added sodium cyanide (1.7 g, 34.7 mmol) at room temperature. The reaction mixture was stirred for five minutes and then manganese (IV) oxide (7.4 g, 85.1 mmol) was added portionwise over a period of 2.5 hours. The reaction mixture was stirred overnight at room temperature under a nitrogen atmosphere. To the reaction mixture was added dichloromethane (75 mL). The reaction mixture was filtered through a pad of Celite^.(R). and the pad was washed with <n="104"/>dichloromethane. The cloudy filtrate was concentrated in vacuo and the residue was partitioned between water and ethyl acetate. The organic phase was separated, washed with water, dried over magnesium sulfate, filtered, and the filtrate was concentrated to give the crude product as an off-white solid. The crude product was purified by flash chromatography over silica gel with a hexanes: ethyl acetate gradient (100:0 to 0: 100) to give 0.636 g (51percent based on recovered starting material) of methyl 6-bromo-lH-indole-3-carboxylate as an off-white solid. ¹H NMR (J₆-DMSO, 400 MHz): δ 12.02 (br s, IH), 8.09 (s, IH), 7.90 (d, J = 9 Hz, IH), 7.65 (d, J = 2 Hz, IH), 7.31 (dd, J = 9, 2 Hz, IH), 3.78 (s, 3H). ES-LCMS m/z 252 (M - H)^".

Reference： [1] Patent: WO2008/157270, 2008, A1, . Location in patent: Page/Page column 102-103

3
[ 101774-27-0 ]
[ 18107-18-1 ]
[ 868656-97-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 20℃; for 0.0333333 h;	Intermediate Preparation 40; 6-Bromo-lH-indole-3-carboxylic acid methyl ester; To a solution of 6-bromoindole-3-carboxylic acid (960 mg, 4.00 mmol) in methanol (9.5 mL) is added (trimethylsilyl)diazomethane (2.0 M solution in hexanes, about 9 mL) over two minutes at room temperature. The yellow mixture is concentrated under reduced pressure. The residue is re-dissolved in methanol and concentrated under reduced pressure. This process is repeated several times to give the title compound as a solid (100percent). ES/MS m/e 256.0 (M + 2).
100%	at 20℃; for 0.0333333 h;	Preparation 13; -Bromo-lH-indole-S-carboxylic acid methyl ester; To a solution of 6-bromoindole-3-carboxylic acid (960 mg, 4.00 mmol) in methanol (9.5 mL) is added (trimethylsilyl)diazomethane (2.0 M solution in hexanes, ca 9 mL) over two minutes at room temperature. The yellow mixture is concentrated under reduced pressure. The residue is redissolved in methanol and concentrated under reduced pressure. This process is repeated several times to give the title compound as a solid (100percent). ES/MS m/e 256.0 (M + 2).

Reference： [1] Patent: WO2009/12125, 2009, A1, . Location in patent: Page/Page column 36
[2] Patent: WO2007/140174, 2007, A2, . Location in patent: Page/Page column 24
[3] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 8, p. 863 - 867

4
[ 67-56-1 ]
[ 101774-27-0 ]
[ 868656-97-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	With hydrogenchloride In water for 2 h; Inert atmosphere; Reflux	To a stirred solution of VII-3 (0.86 g, 3.6 mmol) in MeOH (30 mL) was added aq. HCl (0.5 mL) under nitrogen. After the addition, the solution was heated to reflux under nitrogen for 2 hours. The solvent was removed by reduced pressure and the residue was added sat. NaHCO₃to adjust to pH=9 and the solution was extracted with DCM, the combine organic layer was dried and concentrated in vacuum to afford VII-4 (0.71 g, 78percent) as a yellow solid which was used for next step directly.
72%	at 65℃;	Step 9; -Bromo-lH-indole-S-carboxylic acid methyl ester; Acetyl chloride (29,43 g, 374 mmol) is added slowly at room temperature to a solution of 6-bromo-indole-3-carboxylic acid (45 g, 187.46 mmol) in 50OmL of methanol and the resulting solution is stirred at 65⁰C overnight. The reaction is cooled to room temperature. A white precipitates appears when cooling. After stirring 2h at room temperature, the solid is filtered off and dried under vacuum. 34.4g (72percent) of the title compound is obtained as a light brown solid. MS (m/e): 254 (M+ 1)

Reference： [1] Patent: US2014/200215, 2014, A1, . Location in patent: Paragraph 0978; 0981
[2] Patent: WO2009/12125, 2009, A1, . Location in patent: Page/Page column 61
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 24, p. 9768 - 9772

5
[ 52415-29-9 ]
[ 868656-97-7 ]

Reference： [1] Patent: US2014/200215, 2014, A1,
[2] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 8, p. 863 - 867
[3] Patent: WO2008/157270, 2008, A1,

6
[ 79878-02-7 ]
[ 868656-97-7 ]

Reference： [1] Patent: US2014/200215, 2014, A1,
[2] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 8, p. 863 - 867

7
[ 771-50-6 ]
[ 868656-97-7 ]

Reference： [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 24, p. 9768 - 9772

[ 868656-97-7 ] Synthesis Path-Downstream 1~15

1
[ 101774-27-0 ]
[ 18107-18-1 ]
[ 868656-97-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	In methanol; hexane; at 20℃; for 0.0333333h;Product distribution / selectivity;	Intermediate Preparation 40; 6-Bromo-lH-indole-3-carboxylic acid methyl ester; To a solution of 6-bromoindole-3-carboxylic acid (960 mg, 4.00 mmol) in methanol (9.5 mL) is added (trimethylsilyl)diazomethane (2.0 M solution in hexanes, about 9 mL) over two minutes at room temperature. The yellow mixture is concentrated under reduced pressure. The residue is re-dissolved in methanol and concentrated under reduced pressure. This process is repeated several times to give the title compound as a solid (100%). ES/MS m/e 256.0 (M + 2).
100%	In methanol; hexanes; at 20℃; for 0.0333333h;	Preparation 13; -Bromo-lH-indole-S-carboxylic acid methyl ester; To a solution of 6-bromoindole-3-carboxylic acid (960 mg, 4.00 mmol) in methanol (9.5 mL) is added (trimethylsilyl)diazomethane (2.0 M solution in hexanes, ca 9 mL) over two minutes at room temperature. The yellow mixture is concentrated under reduced pressure. The residue is redissolved in methanol and concentrated under reduced pressure. This process is repeated several times to give the title compound as a solid (100%). ES/MS m/e 256.0 (M + 2).

Reference： [1]Patent: WO2009/12125,2009,A1 .Location in patent: Page/Page column 36
[2]Patent: WO2007/140174,2007,A2 .Location in patent: Page/Page column 24
[3]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 863 - 867

2
[ 67-56-1 ]
[ 101774-27-0 ]
[ 18107-18-1 ]
[ 868656-97-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	In hexanes; at 20℃; for 0.0333333h;	Preparation 39 6-Bromo-lH-indole-3-carboxylic acid methyl esterTo a solution of 6-bromoindole-3-carboxylic acid (960 mg, 4.00 mmol) in methanol (9.5 mL) is added (trimethylsilyl)diazomethane (2.0 M solution in hexanes, approximately 9 mL) over two minutes at room temperature. The yellow mixture is concentrated under reduced pressure. The residue is redissolved in methanol and concentrated under reduced pressure several times to give the title compound as a solid (100%). ES/MS m/e 256.0 (M+2).

Reference： [1]Patent: WO2007/140183,2007,A1 .Location in patent: Page/Page column 36

3
[ 868656-97-7 ]
[ 946427-03-8 ]
6-(4-hydroxy-2-methyl-phenyl)-1H-indole-3-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; N,N-dimethyl-formamide; at 100℃; for 60h;	Preparation 40 6-(4-Hydroxy-2-methyl-phenyl)-lH-indole-3-carboxylic acid methyl esterA mixture of 3-methyl-4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenol (213 mg, 0.910 mmol), -bromo-lH-indole-S-carboxylic acid methyl ester (193 mg, 0.759 mmol), tetrakis(triphenylphosphine)palladium(0) (57 mg, 0.046 mmol), DMF (2.7 mL), ethanol (1.34 mL) and 2M aqueous potassium carbonate (1.34 mL) is heated to 100 0C for 60 hours. The reaction is cooled to room temperature, diluted with water and acidified with 1 N HCl. The resulting solution is extracted with ethyl acetate. The combined organic layers are dried over anhydrous magnesium sulfate and concentrated. <n="38"/>The residue is purified with flash chromatography eluting with 25to 40 % ethyl acetate/heptane to give the title compound (134 mg, 63%). ES/MS m/e 280.3 (M-I).

Reference： [1]Patent: WO2007/140183,2007,A1 .Location in patent: Page/Page column 36-37

5
[ 868656-97-7 ]
[ 74-88-4 ]
6-bromo-1-methyl-1H-indole-3-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2h;	Preparation 12 6-Bromo-l -methyl- lH-indole-3-carboxylic acid methyl esterTo a room temperature mixture of 5-bromo-lH-indole-3-carboxylic acid methyl ester (100 mg, 0.394 mmol), potassium carbonate (163 mg, 1.18 mmol) and DMF is added iodomethane (30 muL, 0.47 mmol). After 1.5 hours, additional iodomethane (10 muL) is added and the reaction is stirred for 30 minutes. The reaction mixture is diluted with dichloromethane and filtered. The filtrate is concentrated under high vacuum, diluted with ethyl acetate, and concentrated to give the title compound (105 mg, 99%). ES/MS m/e 270.0 (M+2).
99%	With potassium carbonate; In N,N-dimethyl-formamide; for 2h;Product distribution / selectivity;	Intermediate Preparation 41; 6-Bromo-l -methyl- IH- indole-3-carboxylic acid methyl ester; To a mixture of 6-bromo- leta-indole-3-carboxylic acid methyl ester (100 mg, 0.394 mmol), potassium carbonate (163 mg, 1.18 mmol) in DMF is added iodomethane (30 muL, 0.47 mmol). The reaction mixture is stirred for 1.5 h. Additional iodomethane (10 muL) is added and the reaction is stirred for 30 minutes. The reaction mixture is diluted with dichloromethane and filtered. The filtrate is concentrated under high vacuum, diluted with ethyl acetate, and concentrated to give the title compound (105 mg, 99%). ES/MS m/e 270.0 (M + 2).
99%	With potassium carbonate; In N,N-dimethyl-formamide; for 2h;	Preparation 14; 6-Bromo-l -methyl- lH-indole-3-carboxylic acid methyl ester; To a mixture of 5-bromo-lH-indole-3-carboxylic acid methyl ester (100 mg, 0.394 mmol), potassium carbonate (163 mg, 1.18 mmol) in DMF is added iodomethane (30 muL, 0.47 mmol). The reaction mixture is stirred for 1.5 hours. Additional iodomethane (10 muL) is added and the reaction is stirred for 30 minutes. The reaction mixture is diluted with dichloromethane and filtered. The filtrate is concentrated under high vacuum, diluted with ethyl acetate, and concentrated to give 105 mg (99%) of the title compound. ES/MS m/e 270.0 (M + 2).

88%	With potassium carbonate; In acetonitrile; at 20℃; for 72h;Product distribution / selectivity;	Step 10; 6-Bromo-l -methyl- lH-indole-3-carboxylic acid methyl ester; To a mixture of 25g (98.39 mmol) of 6-bromo-lH-indole-3-carboxylic acid methyl ester and 27.2Og (196 mmol) of potassium carbonate in 30OmL of acetonitrile is added at room temperature Methyl Iodide (20.95g, 147.6 mmol). The reaction mixture is stirred at room temperature for 3 days. The solvent is evaporated, 500 ml of water is <n="63"/>added, and the organic layer is extracted with (3X300 ml) ethyl acetate. The organics are combined, dried over magnesium sulfate and evaporated. The crude is purified by silica gel chromatography eluting with hex/EtOAc 8:2. The title compound (23.3g (88%)) is obtained as a brown solid. MS (m/e): 268 (M+ 1).
	With potassium carbonate; In N,N-dimethyl-formamide; at 25℃; for 6h;	4-3 (400 mg, 1.57 mmol) and potassium carbonate (653 mg, 4.7 mmol) were dissolved in N,N-dimethylformamide (5 mL), and iodomethane (2.9 g, 20.4 mmol, 1.27 mL) was added. The reaction mixture was stirred at 25 C for 6 hours. Dichloromethane (20 ml) was added to the reaction mixture, and then filtered. The filtrate was concentrated to obtain a residue, to which petroleum ether/ethyl acetate (10/1, 10 mL) was added, and filtered. The obtained solid was dried under vacuum, to give the target compound 4-4 without purification. 1H NMR (400MHz, CHLOROFORM-d) delta 8.02 (d, J = 8.5 Hz, 1H), 7.73 (s, 1H), 7.50 (d, J = 1.3 Hz, 1H), 7.37 (dd, J = 1.8, 8.5 Hz, 1H), 3.93 - 3.87 (m, 3H), 3.84 - 3.75 (m, 3H).

Reference： [1]Patent: WO2007/92751,2007,A2 .Location in patent: Page/Page column 16
[2]Patent: WO2009/12125,2009,A1 .Location in patent: Page/Page column 37
[3]Patent: WO2007/140174,2007,A2 .Location in patent: Page/Page column 24
[4]Patent: WO2009/12125,2009,A1 .Location in patent: Page/Page column 61-62
[5]Journal of Medicinal Chemistry,2015,vol. 58,p. 9768 - 9772
[6]Patent: EP3632910,2020,A1 .Location in patent: Paragraph 0185

6
[ 868656-97-7 ]
[ 18107-18-1 ]
6-bromo-1-(2-dimethylamino-ethyl)-1H-indole-3-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%		Preparation 14 6-Bromo-l-(2-dimethylamino-ethyl)-lH-indole-3-carboxylic acid methyl esterA mixture of -bromo-lH-indole-S-carboxylic acid methyl ester (500 mg, 1.97 mmol), sodium hydride (60% in mineral oil, 748 mg, 31.2 mmol), sodium iodide (295 mg, 1.96 mmol), 2- dimethylaminoethyl chloride hydrochloride (341 mg, 2.37 mmol) and DMF (60 mL) is heated at 100 0C for <n="18"/>8 hours. The reaction mixture is cooled, filtered, and the solids are washed with water and air dried. The solids are dissolved in MeOH (200 mL) and (trimethylsilyl)diazomethane (2.0 M solution in hexanes, 20 mL) is added over several minutes. The reaction mixture is stirred for one hour and concentrated under reduced pressure. The residue is partitioned between water and ethyl acetate. The ethyl acetate layer is separated and dried over MgSO4. The crude product is purified via radial chromatography using 2.5% MeOH/CH2Cl2 to afford the title compound (195 mg, 30%). ES/MS m/e 327.0 (M+2).

Reference： [1]Patent: WO2007/92751,2007,A2 .Location in patent: Page/Page column 16-17

7
[ 868656-97-7 ]
[ 616-38-6 ]
6-bromo-1-methyl-1H-indole-3-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium carbonate; In N,N-dimethyl-formamide; at 130℃;Product distribution / selectivity;	Alternate procedure: Add dimethyl carbonate (1.3 L, 12.4 mol) to a mixture of 6- bromo-lH-indole-3-carboxylic acid methyl ester (1.3 kg, 5.1 mol) and potassium carbonate (1.41 kg, 10.2 mol) in DMF (6.0 L) at room temperature. Heat the mixture to 130 0C and stir overnight. Cool the reaction mixture to ~3 0C and add ice-cold water (6 L). Filter the resulting solid, wash with methanol (2 L) and dry in a vacuum oven to afford 1.1 kg (82%) of the title compound.

Reference： [1]Patent: WO2009/12125,2009,A1 .Location in patent: Page/Page column 62

8
[ 67-56-1 ]
[ 101774-27-0 ]
[ 868656-97-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	With hydrogenchloride; In water; for 2h;Inert atmosphere; Reflux;	To a stirred solution of VII-3 (0.86 g, 3.6 mmol) in MeOH (30 mL) was added aq. HCl (0.5 mL) under nitrogen. After the addition, the solution was heated to reflux under nitrogen for 2 hours. The solvent was removed by reduced pressure and the residue was added sat. NaHCO3 to adjust to pH=9 and the solution was extracted with DCM, the combine organic layer was dried and concentrated in vacuum to afford VII-4 (0.71 g, 78%) as a yellow solid which was used for next step directly.
72%	With acetyl chloride; at 65℃;Product distribution / selectivity;	Step 9; -Bromo-lH-indole-S-carboxylic acid methyl ester; Acetyl chloride (29,43 g, 374 mmol) is added slowly at room temperature to a solution of 6-bromo-indole-3-carboxylic acid (45 g, 187.46 mmol) in 50OmL of methanol and the resulting solution is stirred at 650C overnight. The reaction is cooled to room temperature. A white precipitates appears when cooling. After stirring 2h at room temperature, the solid is filtered off and dried under vacuum. 34.4g (72%) of the title compound is obtained as a light brown solid. MS (m/e): 254 (M+ 1)
	With sulfuric acid; at 60℃; for 24h;	4-2 (8.0 g, 33.3 mmol) was dissolved in methanol (20 mL), and concentrated sulfuric acid (32.7 mg, 333.3 mumol, 18 muL, two drops) was added. The reaction mixture was stirred at 60 C for 24 hours, concentrated to remove the solvent. The residue was purified by column chromatography to give the target compound 4-3. 1H NMR (400MHz, CHLOROFORM-d) delta 8.60 (br. s., 1H), 8.05 (d, J = 8.5 Hz, 1H), 7.90 (d, J = 3.0 Hz, 1H), 7.63 - 7.56 (m, 1H), 7.43 - 7.35 (m, 1H), 3.98 - 3.85 (m, 3H).

Reference： [1]Patent: US2014/200215,2014,A1 .Location in patent: Paragraph 0978; 0981
[2]Patent: WO2009/12125,2009,A1 .Location in patent: Page/Page column 61
[3]Journal of Medicinal Chemistry,2015,vol. 58,p. 9768 - 9772
[4]Patent: EP3632910,2020,A1 .Location in patent: Paragraph 0184

9
[ 52415-29-9 ]
[ 868656-97-7 ]

Reference： [1]Patent: US2014/200215,2014,A1
[2]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 863 - 867
[3]Patent: WO2008/157270,2008,A1

10
[ 868656-97-7 ]
[ 351019-18-6 ]
[ 1093631-88-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; for 15h;Inert atmosphere; Reflux;	13c) Methyl 6-(6-fluoro-3-pyridinyl)-lH-indole-3-carboxylateMethyl 6-bromo-lH-indole-3-carboxylate (0.63 g, 2.48 mmol), 2- fluoropyridyl-5-boronic acid (0.435 g, 3.09 mmol), tetrakistriphenylphosphine palladium (0) (0.14 g, 0.012 mmol), 2 M sodium carbonate (5 mL, 10 mmol), and 1,2- dimethoxyethane (20 mL) were combined and heated at reflux with stirring under a nitrogen atmosphere for 15 hours. The reaction mixture was allowed to cool at room temperature and partitioned between water and ethyl acetate. The organic phase was separated, dried over magnesium sulfate, filtered, and the filtrate was concentrated to give the crude product as a yellow solid. The crude product was purified by flash chromatography over silica gel with a dichloromethane methanol gradient (100:0 to 97:3) to give 0.606 g of methyl 6-(6-fluoro-3-pyridinyl)-lH-indole-3-carboxylate as a yellow solid. 1H NMR indicates that a minor impurity is present. The compound was used without further purification. 1H NMR (J6-DMSO, 400 MHz): delta 12.09 (br s, IH), 8.54 (d, J = 2 Hz, IH), 8.28 (dt, J = 8, 3 Hz, IH), 8.13 (d, J = 3 Hz, IH), 8.06 (d, J = 8 Hz, IH), 7.73 (s, IH), 7.51 (dd, J = 8, 2 Hz, IH), 7.27 (dd, J = 9, 3 Hz, IH), 3.80 (s, 3H). ES-LCMS m/z 269 (M - H)".

Reference： [1]Patent: WO2008/157270,2008,A1 .Location in patent: Page/Page column 103

11
[ 868656-97-7 ]
[ 1093631-89-0 ]

Reference： [1]Patent: WO2008/157270,2008,A1

12
[ 868656-97-7 ]
[ 1093631-54-9 ]

Reference： [1]Patent: WO2008/157270,2008,A1

13
[ 67-56-1 ]
[ 17826-04-9 ]
[ 868656-97-7 ]

Yield	Reaction Conditions	Operation in experiment
51%		13b) Methyl -bromo-lH-indole-S-carboxylateTo a stirred solution of -bromo-lH-indole-S-carbaldehyde (1.6 g, 7.1 mmol) in methanol (70 mL) was added sodium cyanide (1.7 g, 34.7 mmol) at room temperature. The reaction mixture was stirred for five minutes and then manganese (IV) oxide (7.4 g, 85.1 mmol) was added portionwise over a period of 2.5 hours. The reaction mixture was stirred overnight at room temperature under a nitrogen atmosphere. To the reaction mixture was added dichloromethane (75 mL). The reaction mixture was filtered through a pad of Celite and the pad was washed with <n="104"/>dichloromethane. The cloudy filtrate was concentrated in vacuo and the residue was partitioned between water and ethyl acetate. The organic phase was separated, washed with water, dried over magnesium sulfate, filtered, and the filtrate was concentrated to give the crude product as an off-white solid. The crude product was purified by flash chromatography over silica gel with a hexanes: ethyl acetate gradient (100:0 to 0: 100) to give 0.636 g (51% based on recovered starting material) of methyl 6-bromo-lH-indole-3-carboxylate as an off-white solid. 1H NMR (J6-DMSO, 400 MHz): delta 12.02 (br s, IH), 8.09 (s, IH), 7.90 (d, J = 9 Hz, IH), 7.65 (d, J = 2 Hz, IH), 7.31 (dd, J = 9, 2 Hz, IH), 3.78 (s, 3H). ES-LCMS m/z 252 (M - H)".

Reference： [1]Patent: WO2008/157270,2008,A1 .Location in patent: Page/Page column 102-103

14
[ 79878-02-7 ]
[ 868656-97-7 ]

Reference： [1]Patent: US2014/200215,2014,A1
[2]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 863 - 867
[3]Patent: EP3632910,2020,A1

15
[ 868656-97-7 ]
[ 177407-39-5 ]
C₁₅H₁₅NO₂ [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 863 - 867

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Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Bouveault-Blanc Reduction ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Ester Cleavage ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Reactions with Organometallic Reagents ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

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