Potassium Phosphate, Tribasic → HCID 59455032, compound

Participants

Reaction Conditions

Reaction Steps

2,3,4,5-Tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole (100 mg, 0.5 mmol) was dissolved in DMF (3 mL). potassium phosphate (212.4 mg, 1 mmol), copper (I) iodide (9.5 mg, 0.05 mmol) and L-proline (11.51 mg, 0.1 mmol) were added. (1-Bromoprop-1-en-2-yl)cyclohexane (121.8 mg, 0.6 mmol) dissolved in DMF (2 mL) was 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 to the reaction mixture. 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 HPLC. Yield: 11 mg. 1H NMR (CD3OD, TFA salt) δ (ppm): 7.24 (s, 1H), 7.06 (d, 1H), 7.0 (d, 1H), 6.25 (s, 1H), 4.70 (m, 1H), 4.35 (m, 1H), 3.82 (m, 1H), 3.48 (m, 1H), 3.10 (s, 3H), 3.04 (m, 2H), 2.42 (s, 3H), 2.10 (m, 1H), 1.90 (s, 3H), 1.65 (m, 2H), 1.60-1.40 (m, 5H), 1.20-1.0 (m, 3H).

Provenance & Evidence