Sodium Bicarbonate → HCID 90281470, compound

Participants

Reaction Conditions

Reaction Steps

A microwave tube was charged with N—((S)-1-(3-bromo-5-(methylsulfonamido)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)-2-((3bS,4aR)-5,5-difluoro-3-(trifluoromethyl)-3b,4,4a,5-tetrahydro-1H-cyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)acetamide (41D, 20 mg, 0.03 mmol), 5-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (12.3 mg, 0.045 mmol) and PdCl2[P(Cy)3]2 (2.2 mg, 0.003 mmol). To the mixture was added 0.6 mL of 1,4-dioxane and 0.09 mL of sodium bicarbonate aqueous solution (1M). The system was purged with argon and then the microwave tube was sealed and the reaction mixture was heated in a microwave synthesizer at 170° C. for 15 min. After cooling, the reaction was partitioned between EtOAc and water. The organic layer was separated and washed with brine, then dried over MgSO4, filtered and concentrated. The residue was purified by reverse phase HPLC eluting with acetonitrile and water (with 0.1% TFA) to afford the title compound. 1H NMR (400 MHz, methanol-d4) δ 8.91-8.48 (m, 1H), 7.40 (dd, J=13.1, 2.6 Hz, 1H), 7.07-5.77 (m, 5H), 5.38-5.02 (m, 1H), 4.85 (s, 2H), 3.29-2.92 (m, 5H), 2.66-1.95 (m, 5H), 1.41 (dd, J=8.1, 6.0 Hz, 1H), 1.10 (m, 1H). MS (m/z) 738.92 [M+H]+.

Provenance & Evidence