反応 #220882

反応方程式

Tributyltin azide

3,5-bis(benzyloxy)-N-(5-cyanopyridin-2-yl)benzamide

→

tetrazole

3,5-bis(benzyloxy)-N-[5-(1H-tetraazol-5-yl)pyridin-2-yl]benzamide

溶媒

toluene

反応条件

後処理

1. 1
   温度The mixture was heated
2. 2
   温度at reflux for 16 hours
3. 3
   温度The suspension was cooled
4. 4
   その他partitioned between ethyl acetate and hydrochloric acid (1M)
5. 5
   濃縮The organic layer was concentrated in vacuo
6. 6
   その他the residue was purified by MPLC on silica MPLC (eluting with 1% methanol/DCM to 15% methanol/DCM)

実験手順

Tributyltin azide (156 μL, 0.57 mmol) was added to a suspension of 3,5-bis(benzyloxy)-N-(5-cyanopyridin-2-yl)benzamide (180 mg, 0.41 mmol) in toluene (3 mL). The mixture was heated at reflux for 16 hours. The suspension was cooled and partitioned between ethyl acetate and hydrochloric acid (1M). The organic layer was concentrated in vacuo and the residue was purified by MPLC on silica MPLC (eluting with 1% methanol/DCM to 15% methanol/DCM). The tetrazole was obtained as a colourless solid (113 mg, 57%). 1H NMR δ (d6-DMSO): 5.19 (4H, s); 6.88 (1H, s); 7.26-7.48 (12H, m); 8.40 (1H, d); 8.46 (1H, dd); 9.04 (1H, s); 11.13 (1H, br s); m/z (LCMS; ESI+) 479 (MH+).

出典