Pyridine → HCID 86611323, compound

HRID 2235095Notes

Reaction equation

HRID 2235095 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[C:12]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]2[CH:31]=[C:30]3[C:26]([CH2:27][CH2:28][NH:29]3)=[CH:25][CH:24]=2)=[O:22])=[CH:16][C:15]=1[C:32]([F:35])([F:34])[F:33])#[N:13].N1C=CC=CC=1>ClCCl>[C:12]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]2[CH:31]=[C:30]3[C:26]([CH2:27][CH2:28][N:29]3[S:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)(=[O:10])=[O:9])=[CH:25][CH:24]=2)=[O:22])=[CH:16][C:15]=1[C:32]([F:35])([F:33])[F:34])#[N:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 179093-Chlorobenzenesulphonyl chlorideHCID 86611322HCID 86611322, compound

Product 1

HCID 86611323HCID 86611323, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloro-benzenesulphonyl chloride (55 mg, 0.26 mmol, 1.1 equiv.) was added to a mixture of crude 2,3-dihydro-1H-indole-6-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amide (70 mg, 0.24 mmol, 1 equiv.) in dichloromethane (2 ml) and pyridine (0.15 mL, 1.9 mmol, 8 equiv.) and the mixture stirred at room temperature for 16 hours. The solvent was removed under a stream of N2 and the residue purified by column chromatography (SiO2, dichloromethane). Fractions were combined to afford 1-(3-chloro-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amide, 81 mg (67% yield). LC @215 nm; Rt 1.74: 94%, m/z (ES+): 547 (M+H+.), δH (400 MHz; d6-DMSO) 11.04 (1H, s), 8.55 (1H, s), 8.36 (1H, d), 8.12-8.26 (5H, m), 7.92 (1H, t), 7.79 (1H, d), 7.45 (1H, d), 4.15 (2H, t), 3.07 (2H, t).

Workup

  1. customThe solvent was removed under a stream of N2
  2. customthe residue purified by column chromatography (SiO2, dichloromethane)

Sources & evidence

ORD record
ord-367210535eda47fe91fe19ba4c7512cc
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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