1,2-Dimethoxyethane → 1-(1,1-Dimethylethyl)-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-6-[6-(4-morpholinyl)-3-pyridinyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Participants

Reaction Steps

The title compound was prepared in the same manner as described in example 74 using 6-chloro-1-(1,1-dimethylethyl)-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (70 mg, 0.174 mmol), [6-(4-morpholinyl)-3-pyridinyl]boronic acid (47.1 mg, 0.226 mmol), DME (3 mL), water (1.00 mL), sodium carbonate (0.261 mL, 0.523 mmol) and PdCl2(dppf)-CH2Cl2 adduct (11.38 mg, 0.014 mmol) wherein the reaction time was 40 min. The crude product was purified by column chromatography (eluent: gradient of 0 to 15% (9:1 MeOH/NH4OH)/DCM). The final product was collected as a solid, 61 mg (65%). LCMS E-S (M+H)=530.0 1H NMR (400 MHz, DMSO-d6) δ ppm 1.78 (s, 9 H), 2.12 (s, 3 H), 2.24 (s, 3 H), 2.38 (s, 3 H), 3.52-3.64 (m, 4 H), 3.68-3.80 (m, 4 H), 4.38 (d, J=5.05 Hz, 2 H), 5.88 (s, 1 H), 6.99 (d, J=9.09 Hz, 1 H), 7.61 (s, 1 H), 8.34 (dd, J=8.84, 2.53 Hz, 1 H), 8.68 (t, J=5.05 Hz, 1 H), 8.97 (d, J=2.27 Hz, 1 H), 11.53 (s, 1H).

Provenance & Evidence