Potassium Carbonate → Ethyl 2-(4-chloro-2-oxopyridin-1(2H)-yl)-4-methyl-1,3-thiazole-5-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	trans-N,N'-dimethyl-1,2-cyclohexanediamine	HCID 2733821	—
Reactant	Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate	HCID 2824057	—
Reactant	HCID 178516186	HCID 178516186	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	Ethyl 2-(4-chloro-2-oxopyridin-1(2H)-yl)-4-methyl-1,3-thiazole-5-carboxylate	HCID 67548707	0.3%

Reaction Conditions

Temperature	100 °C

Reaction Steps

4-Chloro-2-hydroxypyridine (500 mg, 3.86 mmol), ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate (1.06 g, 4.24 mmol), potassium carbonate (1.06 g, 7.67 mmol) and copper (I) iodide (73 mg, 0.38 mmol) were suspended in DMF (4 mL). trans(±)-N,N′-Dimethylcyclohexane-1,2-diamine (82 mg, 0.58 mmol) was added, and the mixture was stirred at 100° C. for five hours. The reaction solution was diluted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1→2/1) to obtain 3.2 mg of the title compound as a white solid (0.3%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08927588B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-046882b0ec624fb58b84438ed1744a4f
Source note	uspto-grants-2015_01