Piperazine → 6-fluoro-1-(phenylsulfonyl)-3-(1-(2-(piperazin-1-yl)ethyl)-1H-pyrazol-4-yl)-1H-indole

HRID 2274809Notes

Reaction equation

HRID 2274809 reaction equation
Br[CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([F:18])=[CH:15][CH:16]=3)[N:11]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:10]=2)[CH:6]=[N:5]1.[NH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>>[F:18][C:14]1[CH:13]=[C:12]2[C:17]([C:9]([C:7]3[CH:6]=[N:5][N:4]([CH2:3][CH2:2][N:28]4[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]4)[CH:8]=3)=[CH:10][N:11]2[S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 4837PiperazineHCID 1180602393-(1-(2-bromoethyl)-1H-pyrazol-4-yl)-6-fluoro-1-(phenylsulfonyl)-1H-indole2×

Product 1

HCID 1180600956-fluoro-1-(phenylsulfonyl)-3-(1-(2-(piperazin-1-yl)ethyl)-1H-pyrazol-4-yl)-1H-indoleYield 68.2%

Procedure

Following the general method as outlined in Example 28, starting from 3-(1-(2-bromoethyl)-1H-pyrazol-4-yl)-6-fluoro-1-(phenylsulfonyl)-1H-indole (Intermediate 22; 100 mg; 0.22 mmol) and piperazine (38 mg; 0.44 mmol), 68 mg (68%) of the title compound was obtained as a yellow solid after purification by preparative TLC (DCM/MeOH=10/1).

Sources & evidence

ORD record
ord-2d58e22e6e9f4e528dec8f2540342f4f
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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