Sodium Carbonate → HCID 44539959, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	N-(6-bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide	HCID 58255750	—
Reactant	3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-benzenediamine	HCID 66617788	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 44539959	HCID 44539959	—

Reaction Conditions

Temperature	150 °C

Reaction Steps

N-(6-Bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide (200 mg), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-benzenediamine (167 mg) (WO2006/005915, page 90-91), Pd(dppf)Cl2 (43 mg) and 2M sodium carbonate (0.890 ml) were charged in 1,4-dioxane (2 ml) and water (2 ml). The reaction vial was sealed and heated under microwave irradiation at 150° C. for 15 min. The reaction was extracted with DCM (3×30 ml). The combined organic layers were evaporated. To a solution of the residue in DMF (3 ml) was added triethylorthoformate (10 ml) and the mixture heated at reflux for 2 h. The solvent was evaporated and the residue dissolved in methanol:DMSO (3 ml, 1:1) and purified by mass directed preparative HPLC (Method A) to give title compound (26 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08658635B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-95aa02e24175454aaeb1d146d5cf8e64
Source note	uspto-grants-2014_02