Sodium hydride → HCID 68816999, compound

Participants

Reaction Conditions

Reaction Steps

(4aS,9bR)-6-Iodo-2,5-dimethyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole (910 mg, 2.7 mmol) was combined with p-tolylthiophenol (426 mg, 3.3 mmol), sodium hydride (132 mg, 3.3 mmol, 60% in oil dispersion), copper iodide (515 mg, 2.7 mmol) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (5 mL) and stirred at 100° C. for 16 hours. The reaction mixture was partitioned between water and CHCl3. The aqueous layer was extracted with CHCl3 (3×20 mL). The combined organics were washed with sat. NaCl (10 mL), water (10 mL), dried (MgSO4) and evaporated. The residue was loaded onto a SCX resin. The resin was washed with 150 mL of MeOH followed by washing with 2.0 M methanolic ammonia. The collected residue was dissolved in CH3CN and 1N HCl/Ether was added until no further precipitation was observed. The solid was filtered and washed with CH3CN affording the title compound (315 mg, 36%) as a white solid. 1H NMR (CD3OD, 300 MHz) δ 7.20 (d, 1H, J=7.7 Hz), 7.14 (d, 1H, J=7.3 Hz), 7.06 (d, 2H, J=8.1 Hz), 6.97 (d, 2H, J=8.4 Hz), 6.82-6.87 (m, 1H), 3.99-4.05 (m, 1H), 3.71-3.80 (m, 1H), 3.15-3.25 (m, 4H), 3.08 (s, 3H), 2.99 (s, 3H), 2.38-2.43 (m, 1H), 2.26 (s, 3H), 1.90-2.03 (m, 1H) ppm.

Provenance & Evidence