Reaction #47796

Reaction equation

4-nitrobenzaldehyde

sodium triacetoxyborohydride

acetic acid

6-aminoindazole

→

title compound

Yield 86.0%

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

Yield 86.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otherthe 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
   FiltrationThe catalyst was filtered off through celite
6. 6
   OtherAfter evaporation of the solvent the residue
7. 7
   Otherwas purified by HPLC

Procedure

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).

Source