1-Bromo-2-methylpropane → HCID 45274608, compound

Participants

Reaction Conditions

Reaction Steps

To 1-{[3-(4-hydroxyphenyl)-1,2,4-oxadiazol-5-yl]methyl}-3,3-diphenylpiperidin-2-one (Example 206, 0.040 g, 0.094 mmol) and potassium carbonate (0.019 g, 0.141 mmol) in N,N-dimethylformamide (0.5 mL) was added 1-bromo-2-methylpropane (0.012 mL, 0.113 mmol) and the reaction heated to 75° C. for 3 hours. The reaction was cooled, loaded onto a GraceResolv™ 12 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=35 mL/minute) over 30 minutes to give the title compound. 1H NMR (300 MHz, CDCl3) δ 8.11-7.94 (m, 2H), 7.39-7.13 (m, 10H), 7.06-6.93 (m, 2H), 4.90 (s, 2H), 3.80 (d, J=6.5, 2H), 3.61 (t, J=6.5, 2H), 2.77-2.62 (m, 2H), 2.13 (dp, J=6.8, 13.4, 1H), 2.01-1.80 (m, 2H), 1.04 (t, J=10.1, 6H); MS (ESI+) m/z 482.3 (M+H)+.

Provenance & Evidence