Sodium Iodide → HCID 57484938, compound

Participants

Reaction Conditions

Reaction Steps

To a 10 mL microwave vial were sequentially added 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 (0.15 g, 0.401 mmol), sodium iodide (0.012 g, 0.080 mmol), zinc (5.25 mg, 0.080 mmol), DMSO (2.5 mL), triethylamine (0.112 mL, 0.802 mmol), and DBU (0.121 mL, 0.802 mmol). The suspension was stirred and degassed with nitrogen for 5 min, forming an emulsion. Next added 2-methyl-3-butyn-2-01 (0.194 mL, 2.006 mmol) and Pd(Ph3P)4 (0.046 g, 0.040 mmol). The stirring contents were heated at 90° C. for 3 hr, and then allowed to cool to room temperature. The reaction mixture was poured into a solution of water and 20% THF/EtOAc, and stirred. The layers were separated, and the organic layer washed with brine. The organic layer was dried over MgSO4, and then filtered through Celite, washing the filter pad with additional EtOAc. The filtrate was concentrated in vacuo and the crude residue dried overnight on a hi-vac pump. The crude product was purified by silica gel chromatography (eluent: gradient: 5-80% of DCM and Chloroform containing 10% 2M Ammonia (in methanol)). The collected product was dried in vacuum oven at 45° C. overnight, to afford the final product as 0.116 g (67% yield). LCMS E-S (M+H)=421.9. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.44-1.55 (m, 12H), 2.13 (s, 3H), 2.20 (s, 3H), 4.35 (d, J=4.80 Hz, 2H), 5.15-5.26 (m, 1H), 5.70 (s, 1H), 5.89 (s, 1H), 7.65 (s, 1H), 8.38 (s, 1H), 8.93 (t, J=4.80 Hz, 1H), 11.55 (s, 1H).

Provenance & Evidence