Cesium carbonate → 2-Methyl-5-(3-sulfamoyl-phenylamino)-thiazole-4-carboxylic acid ethyl ester

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	3-Bromobenzene-1-sulfonamide	HCID 2734765	—
Reactant	Ethyl 5-amino-2-methylthiazole-4-carboxylate	HCID 13329095	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-Methyl-5-(3-sulfamoyl-phenylamino)-thiazole-4-carboxylic acid ethyl ester	HCID 67549553	24%

Reaction Steps

A microwave vial was charged with 5-amino-2-methyl-thiazole-4-carboxylic acid ethyl ester (0.300 g, 1.61 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (0.28 g, 0.48 mmol) and palladium dibenzylideneacetone (Pd2dba3)-chloroform complex (0.17 g, 0.16 mmol). Degassed dioxane (15.00 ml) was added, followed by 3-bromobenzenesulfonamide (0.38 g, 1.61 mmol) and cesium carbonate (0.93 g, 2.87 mmol) The vial was then irradiated in a microwave oven at 150° C. for 15 min. The mixture was diluted with THF and the solids filtered, washing with THF. The filtrate was evaporated and the residue purified by flash chromatography (heptane ethyl acetate) to yield 2-methyl-5-(3-sulfamoyl-phenylamino)-thiazole-4-carboxylic acid ethyl ester (0.13 g, 24%) as an off-white solid, MS (ISP): m/e=342.1 (M+H+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07678815B2
Source dataset	uspto-grants-2010_03
ORD ID	ord-6561df1085d546689313b22144e807ab
Source note	uspto-grants-2010_03