Sodium hydride → (6-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(4-methanesulfonyl-phenyl)carbamic acid tert-butyl ester

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To (4-methanesulfonyl-phenyl)carbamic acid tert-butyl ester (280 mg) in dry THF (3 ml) was added sodium hydride (60% wt suspension in mineral oil, 1.4 equiv., 33.3 mg) at 0° C. After the effervescence ceased, added 4,6-dichloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine 5 (113 mg) and the reaction mixture was allowed to warm up to room temperature overnight. DCM/brine extraction gave crude (6-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(4-methanesulfonyl-phenyl)carbamic acid tert-butyl ester, which was reacted with indazole boronic acid pinacol ester in General Procedure A to give 142 as a beige solid (118 mg). NMR (d6-DMSO): 3.24 (3H, s), 4.15 (3H, s), 7.56 (1H, t), 7.74 (1H, d), 8.01 (2H, d), 8.28 (2H, d), 8.32 (1H, d), 8.41 (1H, s), 8.99 (1H, s), 10.54 (1H, br), 13.25 (1H, br). MS: MH+ 420.13

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