반응 #47796

반응 방정식

4-nitrobenzaldehyde

sodium triacetoxyborohydride

acetic acid

6-aminoindazole

→

title compound

수율 86.0%

N-(4-aminobenzyl)amino-1H-benzimidazole

수율 86.0%

용매

dichloromethane

반응 조건

후처리

1. 1
   기타the solvent was evaporated
2. 2
   workup.DISSOLUTIONThe resulting residue was dissolved in 10 ml of ethanol
3. 3
   workup.ADDITION20 mg of 10% palladium on carbon was added
4. 4
   workup.STIRRINGstirred under hydrogen atmosphere overnight
5. 5
   여과The catalyst was filtered off through celite
6. 6
   기타After evaporation of the solvent the residue
7. 7
   기타was purified by HPLC

실험 절차

To the solution of 0.145 g (0.98 mmol) of 4-nitrobenzaldehyde in 3 ml of dichloromethane was added 0.31 g (1.47 mmol) of sodium triacetoxyborohydride, 0.6 ml (0.98 mmol) of acetic acid and 0.13 g (0.98 mmol) of 6-aminoindazole. After stirring the mixture overnight at room temperature, the solvent was evaporated. The resulting residue was dissolved in 10 ml of ethanol, 20 mg of 10% palladium on carbon was added and stirred under hydrogen atmosphere overnight. The catalyst was filtered off through celite. After evaporation of the solvent the residue was purified by HPLC and lyophilized to yield 0.2 g (86%) of the title compound. 1H-NMR (CDCl3) δ: 4.12 (2H, br), 6.50-6.70 (5H, m), 7.52 (1H, d), 7.86-7.94 (2H, m), 8.18 (1H, br), 8.29 (1H, br).

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