Water → HCID 56597292, 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 (3-aminophenyl)boronic acid (46.9 mg, 0.34 mmol) in DME/water (3 ml:1 ml). PdCl2(dppf)-CH2Cl2 adduct (8.74 mg, 0.01 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 reaction mixture was irradiated (microwave) at 150° C. for 25 min. After cooling, 2 mL of water was added to the black mixture and solids that precipitated were filtered. DCM/MeOH (1:1) was added, the mixture was pre-absorbed on silica gel and purified by silica gel chromatography (eluent: gradient 0 to 90:10:1 DCM/MeOH/NH4OH). The isolated product was treated with EtOH/EtOAc/hexanes (1:1:1). The solids that precipitated were filtered and dried to afford the title compound (40 mg, 42%) as a light grey solid. LCMS E-S (M+H)=431.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.56 (br. s., 1H), 8.96 (t, J=4.93 Hz, 1H), 8.34 (s, 1H), 8.02 (s, 1H), 7.46 (t, J=1.89 Hz, 1H), 7.36 (d, J=7.58 Hz, 1H), 7.18 (t, J=7.71 Hz, 1H), 6.69 (dd, J=7.83, 1.52 Hz, 1H), 5.90 (s, 1H), 5.25-5.37 (m, 3H), 4.40 (d, J=4.80 Hz, 2H), 2.22 (s, 3H), 2.13 (s, 3H), 1.55 (s, 3H), 1.54 (s, 3H).

Provenance & Evidence