Sodium Bicarbonate → HCID 71268745, compound

Participants

Reaction Conditions

Reaction Steps

In a 25 mL sealable tube under nitrogen were combined 6-bromo-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-indazole-4-carboxamide (120 mg, 0.29 mmol) and 3-pyridinylboronic acid (53 mg, 0.43 mmol) in DME/water (3 mL: 1 mL). PdCl2(dppf)-CH2Cl2 (11.7 mg, 0.014 mmol) was added and the resulting mixture was degassed with nitrogen for 10 min. Sodium bicarbonate (72.5 mg, 0.86 mmol) was added and the insoluble mixture was heated in a microwave at 120° C. for 20 min. It was evaporated and the residue was dissolved in DCM and purified by SiO2 chromatography (eluent: gradient 100% DCM to 80:20:2 DCM/MeOH/NH4OH). Fractions were evaporated. DMF was added along with some water and the solids that precipitated were filtered, washed with water and hexanes and dried to afford the title compound (74 mg, 61%) as a light grey solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.54 (s, 1H) 9.11 (d, J=2.02 Hz, 1H) 8.66 (t, J=4.80 Hz, 1H) 8.61 (dd, J=4.80, 1.26 Hz, 1H) 8.42 (s, 1H) 8.28 (dt, J=8.02, 1.93 Hz, 1H) 8.25 (s, 1H) 7.93 (s, 1H) 7.54 (dd, J=7.83, 4.80 Hz, 1H) 5.89 (s, 1H) 5.19 (dt, J=13.14, 6.57 Hz, 1H) 4.40 (d, J=4.80 Hz, 2H) 2.22 (s, 3H) 2.12 (s, 3H) 1.52 (s, 3H) 1.50 (s, 3H). MS(ES) [M+H]+ 416.1.

Provenance & Evidence