반응 #327944

반응 방정식

sodium azide

sodium ascorbate

L-proline

sodium carbonate

3-phenyl-1-propyne

indazole

Sodium hydroxide

→

title compound

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

용매

water

dimethyl sulfoxide

ethyl acetate

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred for 30 minutes
2. 2
   세척washed with 1 N hydrochloric acid
3. 3
   농축The organic layer was concentrated under reduced pressure
4. 4
   기타the resulting residue was triturated with methanol
5. 5
   기타The remaining solids were absorbed on silica gel
6. 6
   기타purified by silica gel chromatography
7. 7
   세척eluting with a gradient of 0-5% methanol in dichloromethane

실험 절차

Example 87A (969 mg, 3.39 mmol), 3-phenyl-1-propyne (392 mg, 3.37 mmol), sodium azide (278 mg, 4.28 mmol), sodium ascorbate (68 mg, 3.43 mmol), sodium carbonate (75 mg, 0.708 mmol), and L-proline (78 mg, 8.98 mmol) were combined in a 1:1 mixture of dimethyl sulfoxide and water (10 mL). Copper(II) sulfate pentahydrate (46 mg, 0.184 mmol) was added and the mixture was stirred at 65° C. for 3 hours. 6 N Sodium hydroxide (1 mL) was added, and the mixture was stirred for 30 minutes to deprotect the indazole. The mixture was diluted with ethyl acetate and washed with 1 N hydrochloric acid. The organic layer was concentrated under reduced pressure, and the resulting residue was triturated with methanol. The remaining solids were absorbed on silica gel and purified by silica gel chromatography eluting with a gradient of 0-5% methanol in dichloromethane to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 13.35 (s, 1H) 8.58 (s, 1H) 8.17-8.27 (m, 1H) 7.86 (d, J=8.82, 2.03 Hz, 1H) 7.67-7.77 (m, 1H) 7.27-7.36 (m, 2H) 7.18-7.27 (m, 1H) 4.10 (s, 1H). MS (ESI+) m/z 276.0 (M+H)+.

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