반응 #327981

반응 방정식

L-proline

sodium carbonate

sodium azide

sodium ascorbate

solution

5-Ethynyl-1H-indazole

iodobenzene

→

title compound

5-(1-phenyl-1H-1,2,3-triazol-4-yl)-1H-indazole

용매

water

water

water

dimethyl sulfoxide

반응 조건

후처리

1. 1
   세척the crude solids were washed with methanol
2. 2
   세척The methanol wash
3. 3
   기타was removed with a pipette
4. 4
   workup.DISSOLUTIONIt was then dissolved in dimethyl sulfoxide
5. 5
   세척eluting with ethyl acetate
6. 6
   workup.ADDITIONThe product containing fractions
7. 7
   농축concentrated in vacuo
8. 8
   workup.ADDITIONtreated with water
9. 9
   세척the solid was washed with water and methanol
10. 10
    기타The washes were removed with a pipette

실험 절차

To a solution of Example 1C (30 mg, 0.21 mmol) in dimethyl sulfoxide (0.25 mL) was added iodobenzene (0.024 mL, 0.21 mmol), a solution of L-proline (5 mg, 0.042 mmol) and sodium carbonate (5 mg, 0.04 mmol) in water (0.1 mL), sodium azide (16 mg, 0.25 mmol), a solution of sodium ascorbate (8 mg, 0.04 mmol) in water (0.05 mL) and a solution of copper (II) sulfate pentahydrate (6 mg, 0.02 mmol) in water (0.05 mL) and the mixture was heated at 65° C. overnight. The mixture was centrifuged, and the crude solids were washed with methanol. The methanol wash was removed with a pipette. It was then dissolved in dimethyl sulfoxide and passed through a silica gel plug eluting with ethyl acetate. The product containing fractions were combined, concentrated in vacuo, and then treated with water. The mixture was centrifuged, and the solid was washed with water and methanol. The washes were removed with a pipette affording the title compound. 1H NMR (400 MHz,) δ ppm 13.17 (s, 1H), 9.28 (s, 1H), 8.34 (s, 1H), 8.17 (s, 1H), 7.96 (m, 3H), 7.65 (m, 3H), 7.52 (m, 1H). MS (ESI) m/z 262 (M+H).

출처