2-Nitrobenzenesulfenyl chloride → N-[1-(3,5-Difluoro-benzyl)-3-(2-nitro-phenylsulfanyl)-1H-indol-6-yl]-acetamide

HRID 1713407Notes

Reaction equation

HRID 1713407 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([F:22])[CH:21]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[CH:13]=2)[CH:8]=[CH:7]1.[N+:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32]Cl)([O-:25])=[O:24]>C(OCC)C>[F:22][C:20]1[CH:19]=[C:4]([CH:3]=[C:2]([F:1])[CH:21]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[CH:13]=2)[C:8]([S:32][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N+:23]([O-:25])=[O:24])=[CH:7]1

Participants

4

Reactant 2

HCID 243192-Nitrobenzenesulfenyl chlorideHCID 66775496N-[1-(3,5-Difluoro-benzyl)-1H-indol-6-yl]-acetamide

Product 1

HCID 59463834N-[1-(3,5-Difluoro-benzyl)-3-(2-nitro-phenylsulfanyl)-1H-indol-6-yl]-acetamideYield 96.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of N-[1-(3,5-Difluoro-benzyl)-1H-indol-6-yl]-acetamide (23.3 mg, 0.08 mmol) in diethyl ether (4 mL) was added 2-nitrobenzenesulfenyl chloride (14.7 mg, 0.09 mmol). The resulting yellow solution was stirred overnight at room temperature. The mixture was concentrated in vacuo and purified over a SiO2 column (heptane/ethyl acetate 9:1) to give the title compound as a yellow solid (35.0 mg, yield=96%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified over a SiO2 column (heptane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-ce39ffeff8e1458ab7011aa600dce848
Source dataset
uspto-grants-2010_09
Patent number
US07795280B2

Reaction notes

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