2-Chlorobenzenesulfonyl chloride → 2-chloro-N-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)benzenesulfonamide

HRID 1189336Notes

Reaction equation

HRID 1189336 reaction equation
[F:1][CH2:2][C:3]1[N:8]=[C:7]([C:9]#[C:10][CH2:11][CH2:12][NH2:13])[CH:6]=[CH:5][CH:4]=1.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21](Cl)(=[O:23])=[O:22]>>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([NH:13][CH2:12][CH2:11][C:10]#[C:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][F:1])[N:8]=1)(=[O:23])=[O:22]

Participants

3

Reactant 2

HCID 761872-Chlorobenzenesulfonyl chlorideHCID 665983324-(6-(Fluoromethyl)pyridin-2-yl)but-3-yn-1-amine

Product 1

HCID 665983832-chloro-N-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)benzenesulfonamideYield 19%

Procedure

The title compound was prepared in accordance with the general method of Example 184, from 4-(6-(fluoromethyl)pyridin-2-yl)but-3-yn-1-amine (39 mg, 0.22 mmol, Example 189(D)) and 2-chlorobenzenesulfonyl chloride (60 mg, 0.28 mmol). The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3) to yield 14.4 mg (41 μmol, 19%) of 2-chloro-N-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)benzenesulfonamide as an orange oil.

Workup

  1. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3)

Sources & evidence

ORD record
ord-a4fe0f5ea891473f99c47fc8530ab86b
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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