Water → N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	1H-Indole-4-boronic acid, pinacol ester	HCID 11322471	—
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-(1H-indol-4-yl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide	HCID 44540980	36.1%

Reaction Conditions

Temperature	150 °C

Reaction Steps

2M Sodium carbonate solution (0.059 ml), Pd(dppf)Cl2 (5 mg), and water (1 ml) were added to solution of N-(6-bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide (40 mg) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (35 mg) (Frontier Scientific) in 1,4-dioxane (1 ml). The reaction vessel was sealed and heated under microwave irradiation at 150° C. for 15 min. After cooling, water (4 ml) was added, and then the mixture was extracted into DCM (3×10 ml). The organic layers were combined and the solvent evaporated. The residue was dissolved in methanol:DMSO (0.5 ml, 1:1) and purified by mass directed preparative HPLC (Method A) to give title compound (16 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08658635B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-ecead1c48cc2455f971aa99bea7926f8
Source note	uspto-grants-2014_02