Potassium Carbonate → HCID 178461054, compound

Participants

Reaction Conditions

Reaction Steps

Pd(PPh3)4 (0.0075 g, 0.0065 mmol) was added to a suspension of N-(3-bromo-1H-pyrazolo[3,4-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (0.031 g, 0.065 mmol), N,N-dimethyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethanamine (0.029 g, 0.098 mmol) and K2CO3 (0.072 g, 0.52 mmol) in MeCN/H2O (4:1, 1 mL). The reaction mixture was heated to 160° C. in a microwave reactor for 30 minutes. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and filtered through GF/F paper. The filter cake was rinsed with ethyl acetate (50 mL). The filtrate was transferred to a separation funnel, and the organic layers were washed with water (3×20 mL). The organic layers were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with DCM/MeOH (10:1), DCM/MeOH (10:1) containing 1% triethylamine to give N-(3-(3-(2-(dimethylamino)ethoxy)phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (0.010 g, 27%) as a solid. 1H NMR (400 MHz, CD3OD) δ 9.0 (s, 1H), 8.7 (s, 1H), 7.7 (m, 1H), 7.6 (m, 2H), 7.5 (m, 1H), 7.2 (m, 1H), 7.1 (d, J=7.0 Hz, 1H), 4.3 (t, J=5.2 Hz, 2H), 3.1 (m, 2H), 3.0 (m, 2H), 2.5 (s, 6H), 1.9 (m, 2H), 1.1 (t, J=7.6 Hz, 3H); m/z (APCI-pos) M+1=559.1.

Provenance & Evidence