3-Bromoquinoline → HCID 53373563, compound

Participants

Reaction Steps

A solution of 2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (500 mg, 2.50 mmol), 3-bromoquinoline (1.040 g, 5.0 mmol), potassium phosphate tribasic (1.325 g, 6.25 mmol), L-proline (87 mg, 0.756 mmol) and copper iodide (143 mg, 0.752 mmol) in DMF (4 mL) was stirred at 150° C. for 14 h. The reaction mixture was diluted with water and extracted with EtOAc (3×50 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was re-crystallized from MeOH-ether (1:99) to afford 2,8-dimethyl-5-quinolin-3-yl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (350 mg). 1H NMR (Freebase, CDCl3) δ (ppm): 9.0 (s, 1H), 8.2 (d, 1H), 8.17 (s, 1H), 7.82 (t, 1H), 7.68 (t, 1H), 7.61 (t, 1H), 7.25 (s, 1H), 7.18 (d, 1H), 7.0 (d, 1H), 3.7 (s, 2H), 2.8 (m, 4H), 2.58 (s, 3H), 2.4 (s, 3H).

Provenance & Evidence