(1-Methyl-1H-indazol-7-yl)boronic acid → HCID 178481734, compound

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Reaction Steps

The title compound was prepared in 69% yield from 4-{1-[4-(tert-butyldimethyl-silanyloxy)-cyclohexyl]-1H-pyrazol-4-yl}-2-chlorofuro[2,3-c]pyridin-7-ylamine and 1-methylindazole-7-boronic acid by a procedure analogous to Example 229. The material was further purified by preparative TLC (5% 7 N ammonia/MeOH:ethyl acetate) instead of trituration. 1H NMR (400 MHz, DMSO-d6): δ 8.24 (s, 1H), 8.23 (s, 1H), 8.03 (s, 1H), 7.98 (dd, J=0.76, 8.08 Hz, 1H), 7.92 (s, 1H), 7.71 (dd, J=1.01, 7.07 Hz, 1H), 7.56 (s, 1H), 7.29 (dd, J=7.20, 7.96 Hz, 1H), 6.41 (br s, 2H), 4.67 (d, J=4.29 Hz, 1H), 4.15 (tt, J=3.95, 11.59 Hz, 1H), 3.91 (s, 3H), 3.46-3.57 (m, 1H), 2.04 (d, J=12.13 Hz, 2H), 1.79-1.98 (m, 4H), 1.30-1.43 (m, 2H); MS (ESI): 428.94 [M+H]+; HPLC tR=2.63 min (ZQ3: polar—5 min).

Provenance & Evidence