2-Methoxyphenylboronic acid → HCID 68662737, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,2-dimethyl-propionic acid 5-bromo-3-iodo-pyrazolo[3,4-b]pyridin-1-ylmethyl ester (5 g, 11.4 mmol), 2-methoxy-phenyl boronic acid (1.7 g, 11.4 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (420 mg, 0.6 mmol) in THF/Acetonitrile/saturated NaHCO3 (10 ml/10 ml/15 ml) was stirred at 60° C. for 4 hours. The mixture was allowed to cool down to room temperature and then extracted with ethyl acetate (3×). The combined organic layers were extracted with brine, dried with Na2SO4, decanted, and concentrated to dryness. Silica gel chromatography of the crude using a gradient of ethyl acetate and hexane afforded 2,2-dimethyl-propionic acid 5-bromo-3-(2-methoxy-phenyl)-indazol-1-ylmethyl ester (3 g, 63% yield). 1H NMR (500 MHz, DMSO-d6) δ 1.08 (s, 9H), 3.85 (s, 3H), 6.45 (s, 2H), 7.10 (m, 1H), 7.23 (d, 1H), 7.50 (m, 1H), 7.59 (d, 1H), 8.42 (s, 1H), 8.73 (s, 1H).

Provenance & Evidence