Dichloromethane → HCID 73603605, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 2-[3-bromo-4-(3,4-dihydro-2H-1-benzopyran-6-yl)-1-methyl-1H-pyrazol-5-yl]-2-(tert-butoxy)acetate (11i) (50 mg, 0.114 mmol), disodium carbonate (36 mg, 0.343 mmol), and bicyclo[2.2.1]hept-2-en-2-ylboronic acid (19 mg, 0.137 mmol) in a mixture of dimethoxyethane (0.45 mL), ethanol (0.19 mL) and water (0.13 mL) was bubbled with nitrogen for 5 minutes. [1,1′-Bis(diphenylphosphino) ferrocene]dichloropalladium(II), complex with dichloromethane (4.7 mg, 0.006 mmol) was added and the reaction mixture was heated at 140° C. for 2 hours. The solution was concentrated in vacuo. Water (2 mL) was added to the residue and the aqueous layer was washed with diethyl ether (2 mL), acidified with 1M hydrochloric acid until pH 3 and extracted with diethyl ether (2×3 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC (dichloromethane/ethyl acetate 45/55+0.5% formic acid) to provide 2-(3-{bicyclo[2.2.1]hept-2-en-2-yl}-4-(3,4-dihydro-2H-1-benzopyran-6-yl)-1-methyl-1H-pyrazol-5-yl)-2-(tert-butoxy)acetic acid (example 15) (30 mg, 0.069 mmol, 60%) as a mixture of diastereoisomers.

Provenance & Evidence