[ CAS No. 227960-12-5 ] {[proInfo.proName]}

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2D 3D

Structure of 227960-12-5 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 227960-12-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 227960-12-5 ]

SDS Specification

Alternatived Products of [ 227960-12-5 ]

Product Details of [ 227960-12-5 ]

CAS No. :	227960-12-5	MDL No. :	MFCD02179412
Formula :	C₁₁H₁₁NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZECAAQDHFZNFPB-UHFFFAOYSA-N
M.W :	189.21	Pubchem ID :	2759866
Synonyms :

Calculated chemistry of [ 227960-12-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.18
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	54.54
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) :	-5.84 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.07
Log Po/w (XLOGP3) :	2.27
Log Po/w (WLOGP) :	2.26
Log Po/w (MLOGP) :	1.67
Log Po/w (SILICOS-IT) :	2.83
Consensus Log Po/w :	2.22

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.79
Solubility :	0.309 mg/ml ; 0.00163 mol/l
Class :	Soluble
Log S (Ali) :	-2.79
Solubility :	0.306 mg/ml ; 0.00162 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.75
Solubility :	0.0337 mg/ml ; 0.000178 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.61

Safety of [ 227960-12-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H312-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 227960-12-5 ]

* 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 [ 227960-12-5 ]
Downstream synthetic route of [ 227960-12-5 ]

[ 227960-12-5 ] Synthesis Path-Upstream 1~9

1
[ 67-56-1 ]
[ 10242-02-1 ]
[ 227960-12-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	at 0 - 20℃; for 9 h; Reflux	General procedure: Following the above procedure, the crude reaction mixture was diluted with MeOH and cooled to 0°C. Then SOCl2 (36 μL, 0.5 mmol) was added and stirred for 3 h at room temperature. Additional MeOH was added and the reaction mixture was heated to reflux for 6 h. The resulting mixture was quenched with H2O and extracted with EtOAc (3x). The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The resulting crude residue was purified by preparative TLC (hexane:EtOAc = 7:3) to afford the desired products 5a-b.

Reference： [1] Heterocycles, 2015, vol. 90, # 2, p. 1196 - 1204

2
[ 124-41-4 ]
[ 227960-12-5 ]

Reference： [1] Patent: WO2008/6794, 2008, A1, . Location in patent: Page/Page column 25

3
[ 79-22-1 ]
[ 227960-12-5 ]

Reference： [1] Organic Letters, 2016, vol. 18, # 15, p. 3918 - 3921

4
[ 614-96-0 ]
[ 227960-12-5 ]

Reference： [1] Patent: US6492406, 2002, B1,
[2] Organic Letters, 2012, vol. 14, # 20, p. 5326 - 5329,4
[3] Organic Letters, 2016, vol. 18, # 15, p. 3918 - 3921

5
[ 10242-02-1 ]
[ 227960-12-5 ]

Reference： [1] Organic Letters, 2012, vol. 14, # 20, p. 5326 - 5329,4

6
[ 227959-99-1 ]
[ 227960-01-2 ]
[ 227960-12-5 ]

Reference： [1] Journal of Organic Chemistry, 1999, vol. 64, # 10, p. 3608 - 3619

7
[ 66783-82-2 ]
[ 227960-12-5 ]

Reference： [1] Synlett, 2015, vol. 26, # 17, p. 2467 - 2471

8
[ 67-56-1 ]
[ 227960-12-5 ]

Reference： [1] Organic Letters, 2012, vol. 14, # 20, p. 5326 - 5329,4

9
[ 583-68-6 ]
[ 124-41-4 ]
[ 814-68-6 ]
[ 227960-12-5 ]

Reference： [1] Journal of Organic Chemistry, 2003, vol. 68, # 15, p. 6011 - 6019

[ 227960-12-5 ] Synthesis Path-Downstream 1~10

1
[ 124-41-4 ]
[ 227960-12-5 ]

Yield	Reaction Conditions	Operation in experiment
		NaOH (0.18g) added to 2,2,2-trichloro-1-(5-methyl-1H-indol-3-yl)ethanone (assume 9.15mmol) in MeOH (45mL) then heated to 8O0C for 2.5h (LCMS indicated no reaction). NaOMe (1g) added and heating continued at 8O0C overnight (LCMS indicated product), total reaction time ~18.5h, ~16h after addition of NaOMe. Cooled to room temp. Concentrated partially. Residue diluted with EtOAc and washed with water, dried(Na2SO4), filtered and cone, to give a brown solid. Residue purified by chromatography on silica gel with hexane + EtOAc (30-50%) to give the title compound (1.3481 g, 78%). LCMS Rt 2.57 min [ES+] 190, [ES-] 188.

Reference： [1]Patent: WO2008/6794,2008,A1 .Location in patent: Page/Page column 25

2
[ 78-77-3 ]
[ 227960-12-5 ]
[ 1001910-72-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 32h;	Description 20Methyl 5-methyl-1 -(2-methylpropyl)-1 H-indole-3-carboxylate (D20)Methyl 5-methyl-IH-indole-S-carboxylate (may be prepared as described in D19) dissolved in DMF. K2CO3 and isobutyl bromide added and mixture heated at 6O0C. Further isobutyl bromide added after ~8h, 24.5h and 3Oh. Reaction stopped after 32h. Partitioned between H2O and Et2O. Layers separated and aqueous phase extracted further with Et2O. Organic layers combined, dried (Na2SO4), filtered and cone, to give a brown oil which was purified by chromatography on silica gel with hexane + EtOAc (5-30%) as eluent to give the title compound (1.107Og). LCMS Rt 3.41 min [ES+] 246.

Reference： [1]Patent: WO2008/6794,2008,A1 .Location in patent: Page/Page column 25

3
[ 614-96-0 ]
[ 227960-12-5 ]

Yield	Reaction Conditions	Operation in experiment
		a 5-methyl-indole-3-carboxylic acid methyl ester The sub-title compound was prepared in a manner analogous to Example 1a) from 5-methyl-1H-indole. 1H NMR (400 MHz, DMSO-d6): delta11.80 (1H, bs); 8.00 (1H, s); 7.79 (1H, t, J 0.8 Hz); 7.35 (1H, d, J 8.4 Hz); 7.02 (1H, dd, J 8.4 and 1.5 Hz); 3.79 (3H, s); 2.40 (3H, s).

Reference： [1]Patent: US6492406,2002,B1
[2]Organic Letters,2012,vol. 14,p. 5326 - 5329,4
[3]Organic Letters,2016,vol. 18,p. 3918 - 3921

4
[ 612-62-4 ]
[ 227960-12-5 ]
3-methoxycarbonyl-5-methyl-1-(quinol-2-yl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		1.63 g (11.8 [MMOL)] of potassium carbonate are added at [25C] under an argon atmosphere to 0.895 g (4.73 [MMOL)] of [3-METHOXYCARBONYL-5-METHYL-1 H-INDOLE] in 10 cm3 of dimethyl sulphoxide. After stirring at [25C] for 0.5 hour, 0.774 g (4.73 [MMOL)] of 2-chloroquinoline is added. After stirring at [100C] for 48 hours, the reaction mixture is cooled and diluted with 100 cm3 ethyl acetate and then washed with 3 times 50 cm3 of water and 25 cm3 of saturated aqueous sodium chloride solution. After separating the phases by settling, the organic phase is dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 1.2 g of a residue which is recrystallised under hot conditions from 30 cm3 of cyclohexane and 6 cm3 of ethyl acetate to give 0. 8 g of [3-METHOXYCARBONYL-5-METHYL-] [1-(QUINOL-2-YL)-1 H-INDOLE] in the form of a white solid melting at [143C.]

Reference： [1]Patent: WO2004/7480,2004,A1 .Location in patent: Page 30-31

5
[ 19493-44-8 ]
[ 227960-12-5 ]
3-methoxycarbonyl-1-(isoquinol-1-yl)-5-methyl-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		1.65 g (11.9 [MMOL)] of potassium carbonate are added at [25C] under an argon atmosphere to 0.900 g (4.75 [MMOL)] of [3-METHOXYCARBONYi-5-METHYL-1 H-INDOLE] in 10 cm3 of dimethyl sulphoxide. After stirring at [25C] for 0.5 hour, 0.677 cm3 (4.75 [MMOL)] of 1-chloroisoquinoline is added. After stirring at [100C] for 48 hours, the reaction mixture is cooled and diluted with 100 cm3 of ethyl acetate and then washed with 3 times 50 cm3 of water and 25 cm3 of saturated aqueous sodium chloride solution. The organic phase is dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 1.50 g of a residue which is purified by flash chromatography [eluent : cyclohexane/ethyl acetate (8/2 by volume)]. After concentrating the fractions to dryness under reduced pressure (2.7 kPa), [1. 4 G OF 3-METHOXYCARBONYL-1- (ISOQUINOL-1-YL)-5-METHYL-1 H-INDOLE] are obtained in the form of a white solid melting at [142C.]

Reference： [1]Patent: WO2004/7480,2004,A1 .Location in patent: Page 28-29

6
[ 102-46-5 ]
[ 227960-12-5 ]
[ 1377936-25-8 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In acetonitrile; at 50℃; for 3h;Reflux;	To a solution of <strong>[227960-12-5]5-methyl-1H-indole-3-methyl carboxylate</strong>, (CAS 227960-12-5) (3 g, 10.58 mmol) in CH3CN (60 mL) was added cesium carbonate (10.3 g, 31.7 mmol) and the suspension was stirred at reflux temperature for 2 hrs. The mixture was then cooled at 50 C. and 4-(chloromethyl)-1,2-dimethylbenzene, (2.7 g, 17.5 mmol) was added slowly. The reaction mixture was stirred at reflux temperature for 1 hr. The reaction was cooled to room temperature and filtered to remove cesium carbonate, concentrated and gave Intermediate 1 (4.8 g).1H NMR (300 MHz, CDCl3) delta: 7.98 (s, 1H), 7.78 (s, 1H), 7.18-7.28 (m, 1H), 7.01-7.13 (m, 2H), 6.84-6.97 (m, 2H), 5.22 (s, 2H), 3.90 (s, 3H), 2.47 (s, 3H), 2.21 (d, 6H).

Reference： [1]Patent: US2012/129829,2012,A1 .Location in patent: Page/Page column 16

7
[ 227960-12-5 ]
[ 1377935-90-4 ]

Reference： [1]Patent: US2012/129829,2012,A1

8
[ 227960-12-5 ]
[ 1377936-27-0 ]

Reference： [1]Patent: US2012/129829,2012,A1

9
[ 227960-12-5 ]
[ 1377936-30-5 ]

Reference： [1]Patent: US2012/129829,2012,A1

10
[ 227960-12-5 ]
[ 1377936-32-7 ]

Reference： [1]Patent: US2012/129829,2012,A1

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[ 227960-12-5 ]

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[ CAS No. 227960-12-5 ] {[proInfo.proName]}

Quality Control of [ 227960-12-5 ]

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Product Details of [ 227960-12-5 ]

Calculated chemistry of [ 227960-12-5 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 227960-12-5 ]

Application In Synthesis of [ 227960-12-5 ]

[ 227960-12-5 ] Synthesis Path-Upstream 1~9

[ 227960-12-5 ] Synthesis Path-Downstream 1~10

Technical Information

Related Functional Groups of [ 227960-12-5 ]

Esters

Related Parent Nucleus of [ 227960-12-5 ]

Indoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 227960-12-5 ]

Related Parent Nucleus of
[ 227960-12-5 ]