1H-Indazole-5-boronic acid pinacol ester → HCID 68541918, compound

Participants

Reaction Steps

The product of Example 9A (481 mg, 2.01 mmol) was coupled with the product of Example 49A (968 mg, 3.96 mmol) according to the procedure of Example 26B. The free base of the title product was purified by chromatography (SiO2, EtOAc/MeOH (with 2 v. % NH3.H2O) (385 mg, 1.19 mmol, yield, 59.5%). It was then treated with fumaric acid (134 mg, 1.2 mmol) in 15 ml EtOAc/EtOH (10:1 v.) at room temperature for 16 hours. The title product was obtained as a solid (414.6 mg, yield, 59.7%). 1H NMR (300 MHz, CD3OD) δ 1.90-2.24 (m, 3H) 2.32-2.47 (m, 1H) 2.61-2.70 (m, 1H) 3.32-3.52 (m, 5H) 3.96 (dd, J=13.73, 8.31 Hz, 1H) 5.53-5.60 (m, 1H) 6.69 (s, 2H) 7.36 (d, J=9.49 Hz, 1H) 7.69 (d, J=8.82 Hz, 1H) 8.08 (dd, J=8.82, 1.70 Hz, 1H) 8.16-8.23 (m, 2H) 8.38 (s, 1H) ppm. MS (DCI/NH3) m/z 322 (M+H)+. Anal. Calculated for C18H19N5O.1.4C4O4H4.0.6H2O: C, 57.30; H, 5.26; N, 14.16. Found: C, 57.24; H, 5.08; N, 14.24.

Provenance & Evidence