Sodium hydride → HCID 86663043, compound

Participants

Reaction Steps

NaH (0.62 g, 15 mmol, 60% oil dispersion) was added to a stirred solution of methyl 2-bromo-7-chloro-5H-pyrido[3,2-b]indole-4-carboxylate (3.5 g, 10.3 mmol) in dry DMF (30 mL) under nitrogen in an ice bath. After 5 min, 1-(chloromethyl)-4-methoxybenzene (1.82 mL, 13 4 mmol) was added and the reaction was removed from the bath and left stirring at RT overnight. The reaction was diluted with EtOAc, washed with water (4×) and then brine. Removal of the solvent followed by step gradient silica gel radial chromatography with hexane containing 25 to 50% DCM afforded impure methyl 2-bromo-7-chloro-5-(4-methoxybenzyl)-5H-pyrido[3,2-b]indole-4-carboxylate (4.0 g) as a light yellow fully solid that was used as such. MS (ESI) m/z 460.95 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 8.31 (1H, d, J=8.24 Hz), 7.69 (1H, s), 7.47 (1H, d, J=1.53 Hz), 7.34 (1H, dd, J=8.39, 1.68 Hz), 6.78-6.82 (2H, m), 6.73-6.76 (2H, m), 5.63 (2H, s), 3.78 (3H, s), 3.73 (3H, s).

Provenance & Evidence