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

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	1,4-Dioxane	HCID 31275	—
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)benzene-1,2-diamine	HCID 66617788	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-[6-(2,3-diaminophenyl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide	HCID 44539937	115.7%

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) (which may be prepared as described in WO2006005915), Pd(dppf)Cl2 (43 mg) and sodium carbonate (890 μl) were added to a microwave vial followed by 1,4-dioxane (2 ml) and water (2 ml). The mixture was heated under microwave irradiation at 150° C. for 15 min. The reaction was diluted with DCM (30 ml) and the layers separated. The aqueous layer was extracted further with DCM (2×30 ml) and the combined organic extracts were evaporated to dryness to give the title compound (250 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08163743B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-ef0cabcffc86481f8efcd62c65e7f95d
Source note	uspto-grants-2012_04