Water → HCID 66795498, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.56 g (3.60 mmol) of N-[(6-{2-[(tert-butylamino)methyl]-1-naphthyl}pyridin-2-yl)methyl]-2,4,6-trimethylaniline in 30 ml of THF 14.5 ml (10.7 mmol) of 0.74 M PhLi in ether was added by vigorous stirring at −78° C. The resulting mixture was heated to room temperature and then stirred for 10 min. Further on, 2 ml of water was added, and the resulting mixture was poured into 50 ml of water. The crude product was extracted with 3×30 ml of ether. The organic extract was washed with water, dried over K2CO3, and then evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: dichloromethane, then dichloromethane-methanol 20/1 vol., then dichloromethane-methanol-triethylamine=100:10:1, vol.). Yield 1.66 g (90%) of orange oil. Anal. calc. for C36H39N3: C, 84.17; H, 7.65; N, 8.18. Found: C, 84.31; H, 7.77; N, 8.05. For 1H NMR (in CDCl3) see FIG. 1—Top spectrum.

Provenance & Evidence