Tetrahydrofuran → Methyl 1-methyl-3-phenyl-1H-indazole-6-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Phenyl dihydrogen orthoborate	HCID 78412	—
Reactant	Methyl 3-iodo-1-methyl-1H-indazole-6-carboxylate	HCID 57931017	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	Methyl 1-methyl-3-phenyl-1H-indazole-6-carboxylate	HCID 57931013	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

In a 100-mL egg plant-type flask, PdCl2(dppf) (178 mg, 0.22 mmol) was added to a THF (20 mL)-water (2 mL) mixed solution of methyl 3-iodo-1-methyl-1H-indazole-6-carboxylate (690 mg, 22 mmol), phenylboric acid (399 mg, 3.27 mmol) and K2CO3 (1.35 g, 9.81 mmol), and stirred overnight at 80° C. in an argon atmosphere. This was diluted with ethyl acetate, washed with water and saturated saline water, dried with sodium sulfate, filtered and concentrated. The resulting crude product was purified through silica gel column chromatography to obtain the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08138197B2
Source dataset	uspto-grants-2012_03
ORD ID	ord-4b4c9fc9a98146f5bc846b0e8d5602d1
Source note	uspto-grants-2012_03