Sodium Iodide → HCID 66604715, compound

Participants

Reaction Steps

1-(Chloromethyl)-4-methoxybenzene (0.72 ml, 5.36 mmol) and sodium iodide (0.80 g, 5 4 mmol) were added to a stirred suspension of methyl 7-chloro-2-(3-fluoro-4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (1.03 g, 2.68 mmol) and K2CO3 (1.11 g, 8.03 mmol) in DMF (10 ml) at RT. After 2 days this was diluted with EtOAc, washed with water (5×) and brine, and then dried with sodium sulfate. Removal of the solvent followed by radial silica gel chromatography (step gradient elution with hexane containing 0 to 50% DCM) afforded impure methyl 7-chloro-2-(3-fluoro-4-methoxyphenyl)-5-(4-methoxybenzyl)-5H-pyrido[3,2-b]indole-4-carboxylate (820 mg, 1.62 mmol, 61% yield) as a yellow solid that was used as such. MS (ESI) m/z 505.29 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 8.38 (2H, d, J=8.24 Hz), 7.92-7.97 (3H, m), 7.85 (1H, dd, J=8.55, 1.22 Hz), 7.46 (1H, s), 7.34 (1H, dd, J=8.24, 1.53 Hz), 7.06 (1H, t, J=8.70 Hz), 6.86 (2H, d, J=8.24 Hz), 6.75 (2H, d, J=8.55 Hz), 5.66 (2H, s), 3.95 (3H, s), 3.81 (3H, s), 3.73 (3H, s).

Provenance & Evidence