2-Nitrobenzenesulfenyl chloride → 1-(3,5-Difluoro-benzyl)-3-(2-nitro-phenylsulfanyl)-1H-indol-6-ylamine

HRID 1713406Notes

Reaction equation

HRID 1713406 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([F:19])[CH:18]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH2:15])[CH:13]=2)[CH:8]=[CH:7]1.[N+:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29]Cl)([O-:22])=[O:21]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([F:19])[CH:18]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH2:15])[CH:13]=2)[C:8]([S:29][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N+:20]([O-:22])=[O:21])=[CH:7]1

Participants

4

Reactant 2

HCID 243192-Nitrobenzenesulfenyl chlorideHCID 667756161-(3,5-Difluoro-benzyl)-1H-indol-6-ylamine

Product 1

HCID 594638551-(3,5-Difluoro-benzyl)-3-(2-nitro-phenylsulfanyl)-1H-indol-6-ylamineYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3,5-Difluoro-benzyl)-1H-indol-6-ylamine (25 mg, 0.1 mmol) in DCM (4 mL) was added 2-nitrobenzenesulfenyl chloride. The resulting yellow solution was stirred at room temperature for 1 hour. The mixture was concentrated in vacuo and purified over a SiO2 column (heptane/ethyl acetate 9:1) to give the title compound as an orange solid (11.6 mg, yield=28%).

Workup

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

Sources & evidence

ORD record
ord-5c9660c07488417696f9632074f236bb
Source dataset
uspto-grants-2010_09
Patent number
US07795280B2

Reaction notes

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