Nitrogen → HCID 59455266, 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 contents stirred for 5 min. L-proline (230 mg, 2.0 mmol) and cuprous iodide (190 mg, 1.0 mmol) were added to the reaction mixture and N2 bubbled into the reaction mixture. 2-Allyl-8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (2.0 g, 10 mmol) was added and the contents heated at 120° C. for 16 h. After completion of reaction (as monitored by TLC) the reaction mixture was concentrated under vacuum and diluted with water. The desired compound was extracted with EtOAc (4×100 mL). The organic layer was dried over sodium sulfate and concentrated under vacuum to obtain the crude product, which was purified by column chromatography [Eluent: 2% MeOH in DCM]. 1H NMR (DMSO, free base) δ (ppm): 8.60 (d, 2H), 8.20 (s, 1H), 7.64 (d, 2H), 7.42 (s, 1H), 7.32 (s, 1H), 7.10 (d, 1H), 6.98 (s, 1H), 4.60 (d, 2H), 3.80 (m, 2H), 2.80 (m, 2H), 2.41 (s, 3H), 1.96 (s, 3H).

Provenance & Evidence