Potassium Carbonate → Ethyl 2-[5-[[(1,1-dimethylethoxy)carbonyl]amino]-4,5,6,7-tetrahydro-1H-indazol-1-yl]-4-methyl-5-thiazolecarboxylate

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	L-Proline	HCID 145742	—
Reactant	Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate	HCID 2824057	—
Reactant	(4,5,6,7-Tetrahydro-1H-indazol-5-yl)-carbamic acid tert-butyl ester	HCID 67316380	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Product	Ethyl 2-[5-[[(1,1-dimethylethoxy)carbonyl]amino]-4,5,6,7-tetrahydro-1H-indazol-1-yl]-4-methyl-5-thiazolecarboxylate	HCID 67548772	23%

Reaction Steps

The same operation as in Example (223a) was performed using tert-butyl 4,5,6,7-tetrahydroindazol-5-ylcarbamate obtained in Example (242b) (246 mg, 1.04 mmol), ethyl 2-bromo-4-methylthiazole-5-carboxylate (519 mg, 2.07 mmol), copper (I) iodide (40 mg, 0.21 mmol), proline (48 mg, 0.42 mmol) and potassium carbonate (431 mg, 3.12 mmol), to obtain 96 mg of ethyl 2-{5-[(tert-butoxycarbonyl)amino]-4,5,6,7-tetrahydro-1H-indazol-1-yl}-4-methyl-1,3-thiazole-5-carboxylate as a pale yellow solid (23%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08536197B2
Source dataset	uspto-grants-2013_09
ORD ID	ord-913a9bf0e36d43a0b4ef000abed42515
Source note	uspto-grants-2013_09