Nitrogen → 2-(1-Benzyl-4-methyl-pyrrolidin-3-yl)-7-(3,6-dihydro-2H-pyran-4-yl)-3H-imidazo[5,1-f][1,2,4]triazin-4-one

Participants

Reaction Conditions

Reaction Steps

To a mixture of compound 6 (100 mg, 0.23 mmol) and 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (145 mg, 0.69 mmol) in DMF (10 mL) was added potassium phosphate (146 mg, dissolved in 1 mL of H2O). The reaction mixture was degassed by purging with N2 for 15 min, before Pd(dppf)2Cl2 (28 mg, 0.035 mmol) and Xantphos (40 mg, 0.069 mmol) were added. The resulting suspension was bubbled with nitrogen for 10 minutes. The reaction mixture was heated to 150° C. under microwave irradiation for one hour. After cooling down, the reaction mixture was diluted with EtOAc (50 mL), and the precipitate was filtered off. The filtrate was washed with brine (50 mL), dried over Na2SO4, filtered and the filtrate was concentrated. The crude product was purified by column chromatography on silica gel (eluting with EtOAc) to afford 7 (50 mg, 55% yield) as a white solid. LC-MS: m/z 393.03 [M+1]+. 1H NMR (400 MHz, CDCl3): δ 7.85 (s, 1H), 7.37˜7.22 (m, 6H), 4.40 (d, J=2.8 Hz, 2H), 3.95˜3.92 (m, 2H), 3.82˜3.79 (d, J=12.6 Hz, 1H), 3.61˜3.58 (d, J=12.6 Hz, 1H), 3.39˜3.37 (m, 1H), 3.00˜2.98 (d, J=10.0 Hz, 1H), 2.76˜2.73 (m, 3H), 2.54˜2.52 (m, 1H), 2.44˜2.42 (m, 1H), 1.95˜1.90 (m, 2H), 1.21 (d, J=7.2 Hz, 3H).

Provenance & Evidence