Sodium Carbonate → HCID 58356438, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	1,4-Dioxane	HCID 31275	—
Reactant	5-Indolylboronic acid	HCID 2734361	—
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	Water	HCID 962	—
Product	HCID 58356438	HCID 58356438	6.7%

Reaction Conditions

Temperature	150 °C

Reaction Steps

N-(6-Bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide (50 mg), Pd(dppf)Cl2 (12 mg), 2M sodium carbonate (0.222 ml), 1,4-dioxane (1 ml) and water (1 ml) were added to 1H-indol-5-ylboronic acid (29 mg) in a microwave vial. The vial was sealed and heated under microwave irradiation at 150° C. for 15 min. The reaction mixture was extracted with DCM (2×20 ml) and then separated, combined organic layers were evaporated to dryness. The residue was dissolved in methanol:DMSO (1 ml, 1:1) and purified by mass directed preparative HPLC (Method A) to give title compound (3.7 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08658635B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-7b17b1daa6ce4b028541c08ec1815db3
Source note	uspto-grants-2014_02