Sodium hydride → HCID 49779380, compound

Participants

Reaction Steps

To a stirred solution of 2-cyclopropyl-8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (500 mg, 2.2 mmol) in DMF (10 mL) was added sodium hydride (264 mg, 6.6 mmol). After stirring for 10 min at RT, 4-(2-methyl-oxiranyl)-pyridine (448 mg, 3.3 mmol) was added and stirring continued for another 16 h. The reaction mixture was poured into ice water and extracted with EtOAc. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated to afford crude material, which was re-crystallized in ether and hexane to yield 1-(2-cyclopropyl-8-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-2-(pyridin-4-yl)propan-2-ol (600 mg). 1H NMR (CD3OD, TFA salt) d (ppm): 8.62 (d, 2H), 8.18 (d, 2H), 7.20 (s, 1H), 6.95 (d, 1H), 6.80 (d, 1H), 4.50 (m, 1H), 4.40 (s, 2H), 4.0 (m, 1H), 3.70 (m, 1H), 3.30 (m, 3H), 3.10 (m, 1H), 2.36 (s, 3H), 1.78 (s, 3H), 1.20 (m, 4H).

Provenance & Evidence