Pyrazole → 4-(2-(1H-pyrazole-1-yl)ethylsulfonyl)benzonitrile

HRID 923077Notes

Reaction equation

HRID 923077 reaction equation
Br[CH2:2][CH2:3][S:4]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1)(=[O:6])=[O:5].[NH:15]1[CH:19]=[CH:18][CH:17]=[N:16]1>>[N:15]1([CH2:2][CH2:3][S:4]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH:19]=[CH:18][CH:17]=[N:16]1

Participants

3

Reactant 2

HCID 1048PyrazoleHCID 668780144-(2-Bromoethylsulfonyl)benzonitrile

Product 1

HCID 668961834-(2-(1H-pyrazole-1-yl)ethylsulfonyl)benzonitrile

Procedure

250 mg of 4-(2-bromoethylsulfonyl)benzonitrile was used in Procedure P with pyrazole to yield 4-(2-(1H-pyrazole-1-yl)ethylsulfonyl)benzonitrile. 300 mg of 4-(2-(1H-pyrazole-1-yl)ethylsulfonyl)benzonitrile was reacted via Procedure T to give 4-(2-(1H-pyrazole-1-yl)ethylsulfonyl)benzoic acid. 75 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 4-(2-(1H-pyrazole-1-yl)ethylsulfonyl)benzoic acid via Procedure G. The product was purified on reverse phase HPLC to yield 4-(2-(1H-pyrazol-1-yl)ethylsulfonyl)-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide. MS (Q1) 467.0 (M)+.

Sources & evidence

ORD record
ord-d3e6f78efc4e4fa6952e3316f70e1845
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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