1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-(Azidomethyl)thieno[3,2-c]pyridine

Participants

Reaction Conditions

Reaction Steps

To a flame-dried round-bottomed flask containing thieno[3,2-c]pyridin-2-ylmethanol (D-3) (3.2 g, 19.4 mmol) was added DPPA (8 g, 6.26 mL, 29.1 mmol) in THF (50 mL). The reaction mixture was stirred for 5 mins and cooled to 0° C., followed by adding DBU (4.43 g, 4 mL, 29.1 mmol) via syringe. The mixture was allowed to stir at reflux overnight. The reaction was then partitioned between water and ethyl ether. The aqueous layer was extracted with ethyl ether. The combined organic layers were washed with brine, dried over Na2SO4, concentrated, and purified by chromatography to afford the product (3.27 g). MS (m/z): 191 (M+1)+.

Provenance & Evidence