Cesium carbonate → HCID 16041748, compound

Participants

Reaction Conditions

Reaction Steps

The bromide compound (2.00 g) produced in Example 9, 5-amino-1-methyl-1H-pyrazole (456 mg), palladium acetate (175 mg), 2-(di-t-butylphosphino)biphenyl (233 mg) and cesium carbonate (1.66 g) were suspended in 1,4-dioxane (20 mL), and heated under reflux at 120° C. for 40 hours. The reaction liquid was filtered through Celite, the residue on the Celite was washed with chloroform, and the filtrate was concentrated under reduced pressure. The resulting residue was purified through silica gel column chromatography (developed with solvents of ethyl acetate/acetone=6/4 and chloroform/methanol=99/1 in order) to obtain the intended compound as a yellow amorphous solid. 1H-NMR (400 MHz, CDCl3) δ: 7.77 (1H, dd, J=8.3, 1.0 Hz), 7.49-7.43 (2H, m), 7.22 (1H, d, J=2.8 Hz), 7.17 (1H, s), 7.08 (1H, dd, J=7.8, 1.0 Hz), 6.97 (1H, dd, J=8.8, 2.8 Hz), 6.91 (1H, d, J=8.8 Hz), 5.97 (1H, d, J=2.0 Hz), 5.42 (1H, s), 4.60-4.52 (1H, m), 4.18-4.10 (1H, m), 4.07 (3H, s), 4.03 (3H, s), 3.68 (3H, s), 3.65-3.55 (1H, m), 3.40-3.29 (1H, m), 2.77 (1H, d, J=16.6 Hz), 2.71 (1H, d, J=16.6 Hz), 2.25-2.15 (1H, m), 2.10-2.02 (1H, m), 1.92-1.79 (2H, m). MS [M+H]+=528.

Provenance & Evidence