Potassium Iodide → HCID 66590184, compound

Participants

Reaction Conditions

Reaction Steps

Potassium iodide (12.48 mg, 0.075 mmol) and sodium carbonate (80 mg, 0.752 mmol) were combined with methyl ethyl ketone (5 mL) and then 2,2-dicyclohexyl-N-[(3aS,4S,6aR)-octahydrocyclopenta[c]pyrrol-4-yl]acetamide (200 mg, 0.601 mmol) from Example 53 was added followed by the addition of (bromomethylene)dibenzene (124 mg, 0.501 mmol). The reaction was heated overnight at 90° C. The reaction mixture was concentrated with a stream of nitrogen and then purified by silica gel chromatography eluting with 2-10% methanol (2 N ammonia)/dichloromethane to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.74 (dd, J=6.7, 15.4, 1H), 7.61 (t, J=6.7, 3H), 7.35 (t, J=7.6, 4H), 7.28-7.23 (m, 3H), 4.42 (dt, J=7.4, 14.4, 1H), 4.16 (s, 1H), 2.96 (qd, J=4.2, 8.0, 1H), 2.63 (dd, J=4.1, 9.8, 1H), 2.57-2.48 (m, 1H), 2.42 (dt, J=9.4, 14.6, 2H), 2.33 (dd, J=3.7, 9.3, 1H), 2.09-1.90 (m, 3H), 1.90-1.80 (m, 3H), 1.79-1.70 (m, 4H), 1.69-1.55 (m, 6H), 1.46 (d, J=14.7, 1H), 1.39 (s, 1H), 1.33-1.00 (m, 8H), 1.00-0.89 (m, 1H); MS (ESI+) m/z 499 (M+H)+.

Provenance & Evidence