Sodium hydride → 6-(2,5-dichlorobenzyl)-1-methyl-1,6-dihydro-3H-furo[3',4':5,6]pyrido[3,4-b]indol-3-one

Participants

Reaction Steps

6-(2,5-Dichlorobenzyl)-1-methyl-1,6-dihydro-3H-furo[3′,4′:5,6]pyrido[3,4-b]indol-3-one was prepared using Method A from 1-methyl-1,6-dihydro-3H-furo[3′,4′:5,6]pyrido[3,4-b]indol-3-one (9 mg, 0.038 mmol), NaH (0.046 mmol, 2 mg of 60 wt. % suspension in mineral oil) and 2,5-dichlorobenzyl chloride (9 mg, 0.046 mmol) in DMF (1 mL). Purification of the crude product by preparative thin layer chromatography with hexane/ether (2:1) as eluent furnished the desired product (5 mg, 33% yield) as a yellow solid. 1H NMR (CDCl3) δ8.93 (s, 1H), 8.09 (d, J=8.0 Hz, 1H), 7.65 (t, J=7.8 Hz, 1H), 7.37-7.46 (m, 3H), 7.16 (d,J=2.2 Hz, 1H), 6.42 (d,J=2.2 Hz, 1H), 6.05 (q,J=6.6 Hz, 1H), 5.70 (s, 2H), 1.92 (d,J=6.6 Hz, 3H); MS (APCI; (M+H)+) m/z 397.

Provenance & Evidence