Nitrogen → HCID 59455184, compound

Participants

Reaction Conditions

Reaction Steps

4-(2-Bromo-1-methyl-vinyl)-pyridine (2.5 g, 13 mmol) and potassium phosphate (4.2 g, 20 mmol) were stirred for 5 min. DMF (20 mL) was added and the solution stirred for 5 min followed by addition of L-proline (230 mg, 2.0 mmol) and cuprous iodide (190 mg, 1.0 mmol). N2 gas was bubbled into the reaction mixture, and 2-Allyl-8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (2.0 g, 10 mmol) was added. The reaction mixture was heated at 120° C. for 16 h. After completion of reaction (as monitored by TLC) the mixture was concentrated under vacuum and diluted with water. The compound was extracted with EtOAc (4×100 mL) and organic layer dried over sodium sulfate, concentrated under vacuum under vacuum. The crude product was purified by column chromatography [Eluent: 2% MeOH in DCM]. 1H NMR (CD3OD, HCl salt) δ (ppm): 8.82 (d, 2H), 8.38 (d, 2H), 7.82 (s, 1H), 7.39 (s, 1H), 7.18 (s, 2H), 6.15 (m, 1H), 5.70 (m, 2H), 4.75 (m, 1H), 4.40 (m, 1H), 4.05 (d, 2H), 3.98 (m, 1H), 3.60 (m, 1H), 3.25 (m, 1H), 3.20 (m, 1H), 2.42 (s, 3H), 2.18 (s, 3H).

Provenance & Evidence