Pyridine → HCID 68698353, compound

HRID 2235101Notes

Reaction equation

HRID 2235101 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([S:9](Cl)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[CH2:15]([O:17][C:18](=[O:40])[C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([C:28]2[CH:36]=[C:35]3[C:31]([CH2:32][CH2:33][NH:34]3)=[C:30]([O:37][CH3:38])[CH:29]=2)=[O:27])=[CH:21][C:20]=1[F:39])[CH3:16].N1C=CC=CC=1>ClCCl>[CH2:15]([O:17][C:18](=[O:40])[C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([C:28]2[CH:36]=[C:35]3[C:31]([CH2:32][CH2:33][N:34]3[S:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:14])([F:13])[F:1])[CH:4]=3)(=[O:11])=[O:10])=[C:30]([O:37][CH3:38])[CH:29]=2)=[O:27])=[CH:21][C:20]=1[F:39])[CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 68697269HCID 68697269, compound

Product 1

HCID 68698353HCID 68698353, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Trifluoromethylbenzenesulphonyl chloride (45.1 mg, 0.18 mmol, 1.1 equiv.) was added to a mixture of crude 2-fluoro-4-[(4-methoxy-2,3-dihydro-1H-indole-6-carbonyl)-amino]-benzoic acid ethyl ester (60 mg, 0.24 mmol, 1 equiv.) and pyridine (0.11 mL, 1.34 mmol, 8 equiv.) in dichloromethane (2 mL) and the mixture was stirred at room temperature for 16 hours. The solvent was removed under a stream of N2 and the residue purified by preparative HPLC to afford 2-fluoro-4-{[4-methoxy-1-(3-trifluoromethyl-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid ethyl ester, 14.4 mg (33% yield). LC @215 nm; Rt 1.73: 100%, m/z (ES+): 567 (M+H+.).

Workup

  1. customThe solvent was removed under a stream of N2
  2. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-87ed784ef7624d9797f15e2b6f210d99
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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