Sodium Carbonate → 4-(5-{[3,3-Bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl]methyl}-1,2,4-oxadiazol-3-yl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

1-((3-(4-Bromophenyl)-1,2,4-oxadiazol-5-yl)methyl)-3,3-bis(4-fluorophenyl)pyrrolidin-2-one (233 mg, 0.457 mmol; Example 235A), palladium(II) acetate (1.025 mg, 4.57 μmol), sodium carbonate (48.4 mg, 0.457 mmol) and potassium hexacyanoferrate(II) trihydrate (42.4 mg, 0.100 mmol) in N,N-dimethylacetamide (2 mL) was placed under nitrogen and heated to 120° C. The reaction was cooled, loaded onto a GraceResolv™ 40 g silica gel column (Grace Davison Discovery Sciences) and the product eluted with a gradient of 5% ethyl acetate/hexanes to 40% ethyl acetate/hexanes (Flow=40 mL/minute) over 40 minutes to give the title compound. 1H NMR (300 MHz, CDCl3) δ 8.08 (d, J=8.4, 2H), 7.78 (d, J=8.4, 2H), 7.38-7.30 (m, 4H), 7.07-6.98 (m, 4H), 4.89 (s, 2H), 3.57 (t, J=6.5, 2H), 2.84 (t, J=6.4, 2H); MS (ESI−) m/z 455.1 (M−H)−.

Provenance & Evidence