Triisopropyl borate → 1-Chloroisoquinoline-7-boronic acid

Participants

Reaction Conditions

Reaction Steps

7-Bromo-1-chloroisoquinoline (1.38 g, 5.69 mmol) in THF (15 mL) under nitrogen, at −78° C. and triisopropyl borate (2.99 g, 15.93 mmol) added, followed by dropwise addition of n-butyllithium (7.11 mL of 1.6M in hexanes, 11.38 mmol). Allowed reaction mixture to warm to −20° C. over 30 minutes and quenched with 1N HCl (30 mL). Added triethylamine to give pH 7, presorbed solution directly onto silica and flash column chromatography on silica gel to give the product as pale yellow solid (0.78 g, 3.8 mmol). 1H NMR (DMSO) δ 8.73 (s, 1H), 8.48 (br s, 2H), 8.35-8.28 (m, 1H), 8.25-8.13 (m, 1H), 8.06-7.92 (m, 1H), 7.91-7.82 (m, 1H). ESI MS (M+1)+: 208, 210 (Cl).

Provenance & Evidence