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[ CAS No. 43142-64-9 ] {[proInfo.proName]}

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Chemical Structure| 43142-64-9
Chemical Structure| 43142-64-9
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Product Details of [ 43142-64-9 ]

CAS No. :43142-64-9 MDL No. :MFCD14715880
Formula : C11H10ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :HPDPSWAIDXFYTE-UHFFFAOYSA-N
M.W : 223.66 Pubchem ID :13166917
Synonyms :

Calculated chemistry of [ 43142-64-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.18
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 59.4
TPSA : 42.09 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.54
Log Po/w (XLOGP3) : 3.23
Log Po/w (WLOGP) : 3.0
Log Po/w (MLOGP) : 2.22
Log Po/w (SILICOS-IT) : 3.34
Consensus Log Po/w : 2.86

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.51
Solubility : 0.0695 mg/ml ; 0.000311 mol/l
Class : Soluble
Log S (Ali) : -3.79
Solubility : 0.0365 mg/ml ; 0.000163 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.39
Solubility : 0.00915 mg/ml ; 0.0000409 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.92

Safety of [ 43142-64-9 ]

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

Application In Synthesis of [ 43142-64-9 ]

* 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.

  • Downstream synthetic route of [ 43142-64-9 ]

[ 43142-64-9 ] Synthesis Path-Downstream   1~12

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  • [ 28899-75-4 ]
YieldReaction ConditionsOperation in experiment
92% A mixture of 111.5 g of 7-chloroindole-2-carboxylate in 31.25 g of 96% sodium hydroxide in 183 ml of methanolAnd 183 ml of water were heated under reflux for 1 hour, cooled to 45 C, and 10% hydrochloric acid was added dropwise to a pH of 3 to 4, and the mixture was sufficiently cooled to obtain 89.7 g of product as an off-white 7-chloroindole- Yield 92%, HPLC content ? 96%
With lithium hydroxide; In ethanol; water; The ester was treated with 1 M lithium hydroxide in ethanol (5 mL) followed by water (3 mL) and stirred at ambient temperature for 18 h. The solution was acidified with 10% hydrochloric acid, diluted with water and extracted with ethyl acetate. The organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated to afford give 7-Chloro-1H-indole-2-carboxylic acid (0.089 9).
With lithium hydroxide; water; In ethanol; at 20℃; for 18h; 2-Chlorophenylhydrazine hydrochloride (0.5 g) in ethanol (25 mL) was treated with [ETHYLPYRUVATE] (0.324 g) and concentrated sulfuric acid (3 drops). The mixture was stirred at ambient temperature for five min and treated with polyphosphoric acid (0.5 g). The mixture was heated at reflux temperature for 24 h whereupon additional polyphosphoric acid (0.5 g) was added and heating continued for a further 48 h. The reaction mixture was cooled to ambient temperature and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water and the pH of the aqueous layer adjusted to neutrality by addition of saturated sodium hydrogen carbonate solution. The organic fraction was separated, washed with brine, dried over magnesium sulfate, filtered, and concentrated. The residue was purified via silica gel chromatography (5-10% ethyl acetate/hexane) to give [7-CHLORO-1 H-] indole-2-carboxylic acid ethyl ester (0.227 g). This material (0.102 g) was used without further purification. The ester was treated with 1 M lithium hydroxide in ethanol (5 mL) followed by water {3 mL) and stirred at ambient temperature for 18 h. The solution was acidified with 10% hydrochloric acid, diluted with water and extracted with ethyl acetate. The organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated to afford give 7- [CHLORO-1 H-INDOLE-2-CARBOXYLIC ACID] (0.089 g). This material (0.089 g), was treated with HATU (0.259 g), HOAT (0.093 g), N, [N-DIISOPROPYLETHYLAMINE] (0.158 mL) and N-methylpiperazine (0.05 mL) in DMF (0. [6] mL) and stirred at ambient temperature for 18 h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with 1 M hydrochloric acid, saturated sodium hydrogencarbonate solution and then brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified via silica gel chromatography (2-10% 2 M ammonia in [METHANOL/DICHLOROMETHANE)] to give the title compound (0.56 g).'H NMR (400 MHz, [CDCI3)] : [8] 9.17 [(BR S, 1 H),] 7.47 (d, J = 8.1 Hz, [1H),] 7.21 (dd, J = 7.6, 0.8 Hz, 1 H), 7.01 (t, J = 7.8 Hz, 1 H), 6.73 (d, J = 2.3 Hz, 1 H), 3.88 {br m, 4H), 2.45 (t, J = 5.1 Hz, 4H), 2.29 (s, 3H).
0.089 g With lithium hydroxide; In ethanol; water; at 20℃; for 18h; 2-Chlorophenylhydrazine hydrochloride (0.5 g) in ethanol (25 mL) was treated with ethylpyruvate (0.324 g) and concentrated sulfuric acid (3 drops). The mixture was stirred at ambient temperature for five min and treated with polyphosphoric acid (0.5 g). The mixture was heated at reflux temperature for 24 h whereupon additional polyphosphoric acid (0.5 g) was added and heating continued for a further 48 h. The reaction mixture was cooled to ambient temperature and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water and the pH of the aqueous layer adjusted to neutrality by addition of saturated sodium hydrogen carbonate solution. The organic fraction was separated, washed with brine, dried over magnesium sulfate, filtered, and concentrated. The residue was purified via silica gel chromatography (5-10% ethyl acetate/hexane) to give 7-Chloro-1 H-indole-2-carboxylic acid ethyl ester (0.227 g). This material (0.102 g) was used without further purification. The ester was treated with 1 M lithium hydroxide in ethanol (5 mL) followed by water (3 mL) and stirred at ambient temperature for 18 h. The solution was acidified with 10% hydrochloric acid, diluted with water and extracted with ethyl acetate. The organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated to afford give 7-Chloro-1H-indole-2-carboxylic acid (0.089 g). This material (0.089 g), was treated with HATU (0.259 g), HOAT (0.093 g), N, N-diisopropylethylamine (0.158 mL) and N-methylpiperazine (0.05 mL) in DMF (0.6 mL) and stirred at ambient temperature for 18 h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with 1 M hydrochloric acid, saturated sodium hydrogencarbonate solution and then brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified via silica gel chromatography (2-10% 2 M ammonia in methanol/ dichloromethane) to give the title compound (0.56 g).
2.85 g (95.8%) With sodium hydroxide; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethanol; REFERENCE EXAMPLE 9 Preparation of 7-chloro-2-indolecarboxylic acid A mixture of 3.40 g (15.2 mmol) of <strong>[43142-64-9]ethyl 7-chloro-2-indolecarboxylate</strong>, 100 ml of 2N sodium hydroxide solution and 100 ml of ethanol was refluxed for an hour. The solvent was then distilled off under reduced pressure. Thereafter ice water was added to the residue and the resulting mixture was acidified with conc. hydrochloric acid and extracted three times with ethyl acetate. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to give 2.85 g (95.8%) of 7-chloro-2-indolecarboxylic acid. 1H NMR (DMSO-d6) delta: 7.04-7.09 (1H, m), 7.19 (1H, d, J=2.0 Hz), 7.30 (1H, dd, J=1.0, 7.6 Hz), 7.62 (1H, d, J=8.3 Hz), 11.9 (1H, br-s), 13.1 (1H, br-s).

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  • [ 77-78-1 ]
  • [ 108797-29-1 ]
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  • [ 128672-36-6 ]
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YieldReaction ConditionsOperation in experiment
26% Ethyl 7-chloroindole-2-carboxylate in 26% yield (2 steps), mp 104-105; NMR delta(CD3SOCD3) 1.35 (t, 3H), 4.35 (q, 2H), 7.05 (t, 1H), 7.25 (s, 1H), 7.35 (d, 12.05 (bs, 1H); M/z (+) 223 (M+).
3.40 g (45.7%) b) Preparation of ethyl 7-chloro-2-indolecarboxylate After 8.00 g (33.2 mmol) of ethyl 2-(2-chlorophenyl)hydrazonopropionate obtained above was added to 20 g of polyphosphoric acid, the mixture was gradually heated to 190 C., which was kept for 5 minutes. The reaction mixture was cooled to 60 C. and water was then added thereto. The mixture was extracted three times with ethyl acetate. The combined extracts were washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 3.40 g (45.7%) of the desired ethyl 7-chloro-2-indolecarboxylate. 1H NMR (CDCl3) delta: 1.40-1.46 (3H, m), 4,43 (2H, dd, J=7.3, 14.2 Hz), 7.09 (1H, t, J=7.9 Hz), 7.25 (1H, d, J=2.3 Hz), 7.32 (1H, dd, J=1.0, 7.6 Hz), 7.58-7.61 (1H, m), 9.02 (1H, br-s).
  • 12
  • [ 43142-64-9 ]
  • [ 107-14-2 ]
  • 7-chloro-1-cyanomethyl-1<i>H</i>-indole-2-carboxylic acid ethyl ester [ No CAS ]
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