Chlorosuccinimide → 2-benzyl-3-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole

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Reaction Conditions

Reaction Steps

To a solution of 2-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-Indazole (200 mg, 0.598 mmol) in THF (2 mL), was added N-chlorosuccinimide (95.9 mg, 0.718 mmol). The mixture was heated at 40° C. for 4 hr, cooled to rt then concentrated to dryness. The crude material was purified by ISCO® chromatography using a gradient of 1-7% EtOAc in hexane to afford the desired product (180.1 mg, 82%). 1H NMR (400 MHz, DMF-d6) δ 7.98 (s, 1H), 7.59 (d, 1H), 7.38-7.28 (m, 4H), 7.22-7.19 (m, 2H), 5.74 (s, 2H), 1.34 (s, 12H); LC-MS m/z [M+H]+ 369.2, RT 3.94 min.

Provenance & Evidence