Water → 4-[(2,2-Dimethylpropyl)(2-propen-1-yl)amino]-2-(trifluoromethyl)benzonitrile

Participants

Reaction Steps

To a slurry of hexanes-washed NaH (0.534 g of a 60% w/w suspension in mineral oil; 13.4 mmol) in dry DMF (10 mL) at 0° C., under N2, was added a solution of 4-[(2,2-dimethylpropyl)amino]-2-(trifluoromethyl)benzonitrile (1.71 g, 6.68 mmol, step A, Example 57) in DMF (4 mL), dropwise over 10 min. The mixture was stirred 15 min and allyl bromide (1.16 mL, 13.4 mmol) was added dropwise over 3 min. The mixture was stirred 1 h at 0° C. and poured into water. The whole was extracted with Et2O (×3). The combined organic portions were washed (water, brine), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 1.82 g of the title compound as a colorless syrup that slowly solidified: MS (El) m/z 296 (M+, 9%), 239 ([M-tBu]+, 100%), 197 (83%), 170 (99%).

Provenance & Evidence