N-bromobutanimide → 5-bromo-N-(4-fluorobenzyl)-3-methylthiophene-2-carboxamide

HRID 1887254Notes

Reaction equation

HRID 1887254 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][NH:7][C:8]([C:10]2[S:11][CH:12]=[CH:13][C:14]=2[CH3:15])=[O:9])=[CH:4][CH:3]=1.C(NC(C1OC=CC=1C)=O)C1C=CC=CC=1.[Br:34]N1C(=O)CCC1=O>>[Br:34][C:12]1[S:11][C:10]([C:8]([NH:7][CH2:6][C:5]2[CH:16]=[CH:17][C:2]([F:1])=[CH:3][CH:4]=2)=[O:9])=[C:14]([CH3:15])[CH:13]=1

Participants

4

Reactant 3

HCID 67184N-bromobutanimideHCID 878870N-benzyl-3-methylfuran-2-carboxamideHCID 5237273N-(4-fluorobenzyl)-3-methylthiophene-2-carboxamide

Product 1

HCID 686162425-bromo-N-(4-fluorobenzyl)-3-methylthiophene-2-carboxamideYield 87%

Procedure

Following the procedure as described in Preparation 19, making variations only as required to use N-(4-fluorobenzyl)-3-methylthiophene-2-carboxamide) in place of N-benzyl-3-methylfuran-2-carboxamide to react with N-bromosuccinimide, 5-bromo-N-(4-fluorobenzyl)-3-methylthiophene-2-carboxamide was obtained as a colorless solid in 87% yield: 1H NMR (300 MHz, CD3CN) δ 7.38-7.32 (m, 2H), 7.10-7.03 (m, 2H), 6.97 (s, 1H), 4.45 (d, J=6.1 Hz, 2H), 2.40 (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-fef10887adce476ab9130c3789d8bfa5
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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