4-Fluorobenzoyl chloride → 4-fluoro-N-methyl-N-(4-(pyridin-2-yl)but-3-ynyl)benzamide

HRID 1189282Notes

Reaction equation

HRID 1189282 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[F:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>>[F:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([N:2]([CH3:1])[CH2:3][CH2:4][C:5]#[C:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)=[O:19])=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 66598286N-methyl-4-(pyridin-2-yl)but-3-yn-1-amine

Product 1

HCID 665984674-fluoro-N-methyl-N-(4-(pyridin-2-yl)but-3-ynyl)benzamideYield 58.8%

Procedure

The title compound was prepared in accordance with the general method of Example 199(D), from N-methyl-4-(pyridin-2-yl)but-3-yn-1-amine (100 mg, 0.62 mmol) and 4-fluorobenzoyl chloride (99 mg, 0.62 mmol). The crude residue was purified over silicagel chromatography (prepacked 10 g silicagel column, DCM/MeOH:98/2 as eluent) to afford 103 mg of 4-fluoro-N-methyl-N-(4-(pyridin-2-yl)but-3-ynyl)benzamide as a brown oil (Yield: 58%).

Workup

  1. customThe crude residue was purified over silicagel chromatography (prepacked 10 g silicagel column, DCM/MeOH:98/2 as eluent)

Sources & evidence

ORD record
ord-11fecf52951e457da8d9589b2b61711d
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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