Potassium Carbonate → N-[6-(5-Isoquinolinyl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Isoquinoline-5-boronic acid	HCID 599474	—
Reactant	N-(6-bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide	HCID 58255750	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	N-[6-(5-Isoquinolinyl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide	HCID 58356445	—

Reaction Conditions

Temperature	150 °C

Reaction Steps

5-Isoquinolinylboronic acid (21 mg), 0.6M potassium carbonate solution (200 μl) and Pd(dppf)Cl2 (10 mg) in 1,4-dioxane (1 ml) were treated with a solution of N-(6-bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide (40 mg) in 1,4-dioxane (1 ml). The reaction vessel was sealed and heated under microwave irradiation at 150° C. for 30 min. After cooling the solvent was removed in vacuo. The sample was redissolved in methanol and loaded onto C18 reverse phase SPE (0.5 g). Product was eluted with acetonitrile/TFA (0.1%) (3×3 ml), and concentrated under a stream of nitrogen using blow down apparatus. Purification by mass directed preparative HPLC (Method C) gave the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08658635B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-6029f44162404e2abec7cf39b4ad8617
Source note	uspto-grants-2014_02