1-Methylpyrrolidine → HCID 25119060, compound

Participants

Reaction Conditions

Reaction Steps

To a Smith-process vial were added 2-methyl-4-(4-methylsulfanyl-phenyl)-1,2,3,4-tetrahydro-isoquinolin-7-ol (305.8 mg, 1.051 mmol), 2-bromo-4-piperidin-1-ylmethyl-pyridine (338.7 mg, 1.314 mmol), Cs2CO3 (684.9 mg, 2.102 mmol) and N-methylpyrrolidine (2.10 mL). The vial was purged with N2, the cap sealed, and the reaction mixture heated at 150° C. in a microwave reactor for 2 h. The mixture was diluted with Et2O, washed with 1 N NaOH, water and brine, dried, and concentrated. Purification by FCC gave the desired product (237.5 mg, 48%). MS (ESI): mass calcd. for C28H33N3OS, 459.23; m/z found, 460.3 [M+H]+. 1H NMR (acetone-d6): 8.03 (d, J=5.1, 1H), 7.23-7.19 (m, 4H), 7.04 (d, J=5.1, 1H), 6.94 (s, 1H), 6.90-6.89 (m, 1H), 6.88-6.83 (m, 2H), 4.19 (t, J=6.2, 1H), 3.63 (q, J=15.1, 2H), 3.46 (s, 2H), 2.92-2.88 (m, 1H), 2.62-2.58 (m, 1H), 2.47 (s, 3H), 2.41-2.35 (m, 4H), 2.35 (s, 3H), 1.56 (quintet, J=5.5, 4H), 1.46-1.40 (m, 2H).

Provenance & Evidence