Pyridine → N-[(4-fluorophenyl)methyl]-2-oxo-1,3-dihydroindole-5-sulfonamide

HRID 49111Notes

Reaction equation

HRID 49111 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)(=[O:4])=[O:3].[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1.N1C=CC=CC=1>ClCCl>[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH:21][S:2]([C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9](=[O:14])[CH2:8]3)(=[O:4])=[O:3])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 673264-FluorobenzylamineHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 9266705N-[(4-fluorophenyl)methyl]-2-oxo-1,3-dihydroindole-5-sulfonamideYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 5-chlorosulfonyl-2-oxindole (5.0 g), 4-fluorobenzylamine (3.0 mL) and pyridine (3.5 mL) in dichloromethane (30 mL) was stirred at room temperature for 4 hours. The precipitate was filtered, washed with dichloromethane and dried to give 5.8 g (84%) of 2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid-4-fluoro-benzylamide.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with dichloromethane
  3. customdried

Sources & evidence

ORD record
ord-b172eca4dae14035b5903c3ea04e30c6
Source dataset
uspto-grants-2004_03
Patent number
US06706709B2

Reaction notes

Loading…