8-chloro-2-methyl-1H,2H,3H,4H,5H-pyrido(4,3-b)indole → HCID 59454887, compound

Participants

Reaction Conditions

Reaction Steps

8-Chloro-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole (110 mg, 0.5 mmol) was dissolved in DMF (3 mL) and potassium phosphate (212.4 mg, 1 mmol), copper (I) iodide (9.5 mg, 0.05 mmol), L-proline (11.51 mg, 0.1 mmol) were added. (1-Bromoprop-1-en-2-yl)cyclohexane (121.8 mg, 0.6 mmol) was dissolved in DMF (2 mL) and added dropwise to it. Nitrogen was purged for 2 min and the reaction mixture was heated at 85° C. overnight (prolonged heating required in some cases). DMF was evaporated and water added. The precipitate obtained was filtered and purified by silica gel chromatography (100-200 mesh) using 0-3% MeOH:DCM as eluent. The compound was further purified through reverse phase purification. Yield: 35 mg. 1H NMR (CD3OD, TFA salt) δ (ppm): 7.50 (s, 1H), 7.18 (m, 2H), 6.28 (s, 1H), 4.70 (m, 1H), 4.58 (m, 1H), 3.82 (m, 1H), 3.60 (m, 1H), 3.15 (s, 3H), 3.10 (m, 2H), 2.0 (m, 1H), 1.90 (s, 3H), 1.70 (m, 2H), 1.58 (m, 1H), 1.50 (m, 4H), 1.15 (m, 3H).

Provenance & Evidence