Potassium Cyanide → 2-(9-(4-fluorobenzyl)-2-methyl-1-oxo-4-(p-tolyl)-2,9-dihydro-1H-pyrido[3,4-b]indol-3-yl)acetonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 9-(4-fluorobenzyl)-3-(hydroxymethyl)-2-methyl-4-(p-tolyl)-2,9-dihydro-1H-pyrido[3,4-b]indol-1-one (125 mg, 0.293 mmol) 1,2-Dichloroethane (DCE) (3 mL) was treated with Thionyl bromide (0.022 mL, 0.293 mmol), heated at 70° C. for 2 hours and then concentrated to dryness. The resultant was dissolved in DMF (2 mL), treated with KCN (76 mg, 1.17 mmol) and then stirred at room temperature overnight. Brine was added and the mixture was extracted with ethyl acetate. The combined extracts were dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel (0-70% ethyl acetate/hexanes) to afford 2-(9-(4-fluorobenzyl)-2-methyl-1-oxo-4-(p-tolyl)-2,9-dihydro-1H-pyrido[3,4-b]indol-3-yl)acetonitrile (110 mg, 0.253 mmol, 86% yield) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) ppm 7.29-7.44 (m, 4H) 7.17-7.24 (m, 1H) 6.91-6.99 (m, 4H) 6.62-6.70 (m, 1H) 6.10-6.16 (m, 2H) 3.90 (s, 3H) 3.67 (s, 2H) 2.51 (s, 3H); LCMS (m/z) ES+=436 (M+1).

Provenance & Evidence