N-bromobutanimide → 5-bromo-N-(3-fluorobenzyl)-3-methylthiophene-2-carboxamide

HRID 1887255Notes

Reaction equation

HRID 1887255 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][NH:6][C:7]([C:9]1[S:10][CH:11]=[CH:12][C:13]=1[CH3:14])=[O:8].C(NC(C1OC=CC=1C)=O)C1C=CC=CC=1.[Br:34]N1C(=O)CCC1=O>>[Br:34][C:11]1[S:10][C:9]([C:7]([NH:6][CH2:5][C:4]2[CH:15]=[CH:16][CH:17]=[C:2]([F:1])[CH:3]=2)=[O:8])=[C:13]([CH3:14])[CH:12]=1

Participants

4

Reactant 3

HCID 67184N-bromobutanimideHCID 878870N-benzyl-3-methylfuran-2-carboxamideHCID 47161045N-(3-fluorobenzyl)-3-methylthiophene-2-carboxamide

Product 1

HCID 686159285-bromo-N-(3-fluorobenzyl)-3-methylthiophene-2-carboxamideYield 89%

Procedure

Following the procedure as described in Preparation 19, making variations only as required to use N-(3-fluorobenzyl)-3-methylthiophene-2-carboxamide) in place of N-benzyl-3-methylfuran-2-carboxamide to react with N-bromosuccinimide, 5-bromo-N-(3-fluorobenzyl)-3-methylthiophene-2-carboxamide was obtained as a colorless solid in 89% yield: 1H NMR (300 MHz, CD3CN) δ 7.39-7.31 (m, 1H), 7.16 (d, J=7.6 Hz, 1H), 7.08 (d, J=10.2 Hz, 1H), 7.02 (dd, J=8.5, 2.5 Hz, 1H), 6.98 (s, 1H), 4.48 (d, J=6.1 Hz, 2H), 2.42 (s, 3H); MS (ES+) m/z 328.1 (M+1), 330.1 (M+1).

Workup

  1. customas described in Preparation 19

Sources & evidence

ORD record
ord-7f5cd02d000a4bd1b8fb4c72c4b1a7f0
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

Loading…