Water → methyl 2-(1-methyl-6-(trifluoromethyl)-1H-indazol-3-yl)-5-(pivaloyloxymethyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	1-methyl-3-(tributylstannyl)-6-(trifluoromethyl)-1H-indazole	HCID 71280492	—
Reactant	methyl 2-bromo-5-(pivaloyloxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylate	HCID 86677991	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Dimethylformamide	HCID 6228	—
Product	methyl 2-(1-methyl-6-(trifluoromethyl)-1H-indazol-3-yl)-5-(pivaloyloxymethyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate	HCID 71279523	50.4%

Reaction Conditions

Temperature	90 °C

Reaction Steps

A mixture of methyl 2-bromo-5-(pivaloyloxymethyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (0.3 g, 0.81 mmol), 1-methyl-3-(tributylstannyl)-6-(trifluoromethyl)-1H-indazole (0.98 g, 1.51 mmol), Pd(PPh3)4 (174 mg, 0.151 mmol) and CuI (58 mg, 0.302 mmol) in dry DMF (10 mL) was heated to 90° C. for 3 hours. Water (10 mL) was added. The formed precipitate was separated by filtration, washed with petroleum ether (3 mL) to afford methyl 2-(1-methyl-6-(trifluoromethyl)-1H-indazol-3-yl)-5-(pivaloyloxymethyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (200 mg, 50%) as a white solid. LCMS: (M+H)+=490.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08658646B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-1262d48d3c7049e2935f69670665f500
Source note	uspto-grants-2014_02