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

HRID 334809Notes

Reaction equation

HRID 334809 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:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18]>>[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([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:18]

Participants

3

Reactant 2

HCID 691102-Chlorobenzoyl chlorideHCID 665983324-(6-(Fluoromethyl)pyridin-2-yl)but-3-yn-1-amine

Product 1

HCID 665981042-chloro-N-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)benzamideYield 19.5%

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-chlorobenzoyl chloride (50 mg, 0.28 mmol). The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3) to yield 13.5 mg (43 μmol, 19%) of 2-chloro-N-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)benzamide as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-c59c10d3aa1c41cc81f1a1f64f591a84
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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