Dichloromethane → 3-benzo[b]furan-2-yl-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	Benzo[b]furan-2-boronic acid	HCID 2776266	—
Reactant	3-Bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carbonitrile	HCID 22479945	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	3-benzo[b]furan-2-yl-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile	HCID 22479858	15%

Reaction Conditions

Temperature	95 °C

Reaction Steps

3-Bromo-1-(tetrahydro-2-pyranyl)-1H-indazole-5-carbonitrile (1.00 g, 3.27 mmol), 2-benzofuranboronic acid (795 mg, 4.90 mmol), Pd(dppf)Cl2.CH2Cl2 (266 mg) and potassium phosphate (3.47 g, 16.35 mmol) in 1,2-dimethoxyethane (16.0 mL) was placed into a screw-top pressure tube and heated in a 95° C. oil bath for 21 h. The reaction mixture was cooled and partitioned between dichloromethane and water. The organic layer was separated, washed with satd. NaHCO3, brine, dried over MgSO4 and concentrated in vacuo to give a residue which was purified by flash chromatography on silica gel with 30% ethyl acetate in hexane (R=0.49) to afford the desired product (167 mg, 15% yield) as a pale orange foam.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06897231B2
Source dataset	uspto-grants-2005_05
ORD ID	ord-b4fd488c87d240a8bcfe391be0094985
Source note	uspto-grants-2005_05