Sodium Bicarbonate → HCID 56598005, compound

Participants

Reaction Steps

In a 25 mL sealable tube under nitrogen were combined 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (80 mg, 0.21 mmol) and (4-aminophenyl)boronic acid (44 mg, 0.32 mmol) in DME/water (3 ml:1 ml). PdCl2(dppf)-CH2Cl2 adduct (8.74 mg, 0.011 mmol) was added and the resulting mixture was degassed with nitrogen for 10 min. Sodium bicarbonate (53.9 mg, 0.64 mmol) was added, the vessel was sealed, and the insoluble light pink mixture was irradiated (microwave) at 150° C. for 30 min. After cooling, DCM/MeOH (1:1) was added, it was pre-absorbed on silica gel and purified by silica gel chromatography (eluent: gradient 0 to 90:10:1 DCM/MeOH/NH4OH). The isolated solid was treated with MeOH. The solids that precipitated were filtered and dried to afford the title compound (63 mg, 66%) as a yellow solid. LCMS E-S (M+H)=431.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.56 (s, 1H), 8.88 (t, J=4.93 Hz, 1H), 8.27 (s, 1H), 8.01 (s, 1H), 7.99 (d, J=2.02 Hz, 2H), 6.69 (s, 1H), 6.67 (s, 1H), 5.90 (s, 1H), 5.61 (s, 2H), 5.24-5.32 (m, 1H), 4.40 (d, J=4.80 Hz, 2H), 2.22 (s, 3H), 2.13 (s, 3H), 1.53 (s, 3H), 1.51 (s, 3H).

Provenance & Evidence