3-Fluorobenzylamine → N-(3-fluorobenzyl)-3-methylthiophene-2-carboxamide

HRID 1887251Notes

Reaction equation

HRID 1887251 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([OH:9])=O.[F:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][NH2:15]>>[F:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][NH:15][C:7]([C:3]1[S:4][CH:5]=[CH:6][C:2]=1[CH3:1])=[O:9]

Participants

3

Reactant 2

HCID 668533-FluorobenzylamineHCID 902693-Methyl-2-thenoic acid

Product 1

HCID 47161045N-(3-fluorobenzyl)-3-methylthiophene-2-carboxamideYield 96%

Procedure

Following the procedure as described in Preparation 18, making variations only as required to use 3-methylthiophene-2-carboxylic acid in place of 3-methylfuran-2-carboxylic acid to react with 3-fluorobenzylamine in place of benzylamine, N-(3-fluorobenzyl)-3-methylthiophene-2-carboxamide was obtained as a colorless solid in 96% yield: 1H NMR (300 MHz, CDCl3) δ 7.35-7.25 (m, 2H), 7.15-6.94 (m, 3H), 6.90 (d, J=5.0 Hz, 1H), 6.14 (br s, 1H), 4.61 (d, J=5.9 Hz, 2H), 2.54 (s, 3H); MS (ES+) m/z 250.2 (M+1).

Workup

  1. customas described in Preparation 18

Sources & evidence

ORD record
ord-d5a59cbe5f134b9f8e6f3685b58541c9
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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