Reaktion #327944

Reaktionsgleichung

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

Lösungsmittel

water

dimethyl sulfoxide

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred for 30 minutes
2. 2
   Waschenwashed with 1 N hydrochloric acid
3. 3
   EinengenThe organic layer was concentrated under reduced pressure
4. 4
   Sonstigethe resulting residue was triturated with methanol
5. 5
   SonstigeThe remaining solids were absorbed on silica gel
6. 6
   Sonstigepurified by silica gel chromatography
7. 7
   Wascheneluting with a gradient of 0-5% methanol in dichloromethane

Vorschrift

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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