2-Bromopyridine → N-(3-chlorophenyl)-N-methyl-5-(pyridin-2-yl)pent-4-ynamide

HRID 1189130Notes

Reaction equation

HRID 1189130 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:8][C:9]1[CH:10]=[C:11]([N:15]([CH3:22])[C:16](=[O:21])[CH2:17][CH2:18][C:19]#[CH:20])[CH:12]=[CH:13][CH:14]=1>>[Cl:8][C:9]1[CH:10]=[C:11]([N:15]([CH3:22])[C:16](=[O:21])[CH2:17][CH2:18][C:19]#[C:20][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:12]=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 79732-BromopyridineHCID 86086853Pent-4-ynoic acid (3-chloro-phenyl)-methyl-amide

Product 1

HCID 66598244N-(3-chlorophenyl)-N-methyl-5-(pyridin-2-yl)pent-4-ynamideYield 33.3%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromopyridine (80 mg, 0.51 mmol) and pent-4-ynoic acid (3-chloro-phenyl)-methyl-amide (113 mg, 0.51 mmol). The crude residue was purified by C18 flash chromatography to yield 51 mg (0.17 mmol, 33%) of N-(3-chlorophenyl)-N-methyl-5-(pyridin-2-yl)pent-4-ynamide as a brown liquid.

Workup

  1. customThe crude residue was purified by C18 flash chromatography

Sources & evidence

ORD record
ord-527a4cd4347a41eb8d1af5135d7f5eed
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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