1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-(Azidomethyl)-2-(trifluoromethyl)pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of (6-(trifluoromethyl)pyridin-3-yl)methanol (2.0 g, 11.3 mmol) and diphenyl phosphorazidate (2.93 mL, 14 mmol) was dissolved in dry toluene (20 mL). The mixture was cooled to 0° C. under Argon, and neat DBU (2.1 mL, 14 mmol) was added. The reaction mixture was stirred for 2 h at 0° C. and then at rt for 16 h. The resulting two-phase mixture was washed with water and extracted with EtOAc. The combined organic layer was concentrated in vacuo and purified by silica gel chromotography afford 5-(azidomethyl)-2-(trifluoromethyl)pyridine (2.3 g, quantitative yield) of a light yellow oil: 1H NMR (300 MHz, CDCl3+CD3OD), d: 8.686 (m, 1H), 7.853 (m, 1H), 7.723 (d, J=8.1 Hz, 1H), 4.518 (s, 2H).

Provenance & Evidence