Diisopropylethylamine → 2-Bromo-1,3-thiazole-5-carboxamide

HRID 12445Notes

Reaction equation

HRID 12445 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:7]([OH:9])=O)=[CH:5][N:6]=1.CC[N:12](C(C)C)C(C)C>>[Br:1][C:2]1[S:3][C:4]([C:7]([NH2:12])=[O:9])=[CH:5][N:6]=1

Participants

3

Reactant 2

HCID 81531DiisopropylethylamineHCID 27632102-Bromothiazole-5-carboxylic acid

Product 1

HCID 203286042-Bromo-1,3-thiazole-5-carboxamide

Procedure

Scheme 1 illustrates the synthesis of compounds of Formula 4 and 5. 2-Bromo-thiazol-5-carboxylic acid 1 is reacted with amine 2 in the presence of DMC and DIEA to afford 2-bromo-thiazol-5-carboxamide 3, which without separation is treated with arylboronic acid under Suzuki coupling conditions to give 2-aryl-thiozol-5-carboxamide 4. Reduction of amide 4 with Alane-N,N-dimethylethylamine complex produces compound 5.

Sources & evidence

ORD record
ord-0eb0e0597917431581e6ff8309ee50c2
Source dataset
uspto-grants-2010_06
Patent number
US07728009B1

Reaction notes

Loading…