Hydrochloric Acid → HCID 89463409, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-(9-(4-fluorobenzyl)-2-methyl-1-oxo-4-(p-tolyl)-2,9-dihydro-1H-pyrido[3,4-b]indol-3-yl)acetonitrile (45 mg, 0.103 mmol) in Ethanol (3 mL) and Water (1 mL) was treated with KOH (5.80 mg, 0.103 mmol) and heated in a sealed tube at 140° C. for 3 days. The mixture was cooled to 0° C. and then treated with 4N HCl until pH<2. The mixture was partly concentrated and then extracted with ethyl acetate. The combined extracts were washed with brine and then concentrated. The residue was dissolved AcOH and concentrated HCl (37%) and irradiated in microwave at 120° C. for 1 hour. The mixture was concentrated to dryness. The residue was diluted with Ethyl acetate, washed with brine, dried over Na2SO4, filtered and concentrated. The resultant was dissolved in Methanol (3.00 mL), cooled to 0° C., treated with TMS-diazomethane (59.0 mg, 0.517 mmol) and then stirred at 0° C. for 20 minutes. The mixture was concentrated and the residue purified on silica gel (0-100% ethyl acetate/hexanes) to afford methyl 2-(9-(4-fluorobenzyl)-2-methyl-1-oxo-4-(p-tolyl)-2,9-dihydro-1H-pyrido[3,4-b]indol-3-yl)acetate (45 mg, 0.096 mmol, 93% yield) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) ppm 7.31-7.42 (m, 4H) 7.22-7.27 (m, 3H) 6.92-7.00 (m, 3H) 6.87-6.92 (m, 1H) 6.61-6.66 (m, 1H) 6.16 (s, 2H) 3.73 (s, 3H) 3.70 (s, 3H) 2.48 (s, 3H); LCMS (m/z) ES+=469 (M+1).

Provenance & Evidence