Reaction #341970

Reaction equation

Sodium triacetoxyl-borohydride

5-bromo-pyridine-3-amine

3-cyclopentyloxy-4-methoxy-benzaldehyde

HOAc

→

5-bromo-N-(3-(cyclopentyloxy)-4-methoxybenzyl)pyridin-3-amine

Yield 93.0%

Solvents

DCE

—

1,2-dichloroethtane

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   WashThe organic phase was washed with water
3. 3
   Dryingdried over sodium sulfate
4. 4
   OtherThe solvent was removed by under reduced pressure

Procedure

Sodium triacetoxyl-borohydride (245 mg, 1.16 mmol) was added to the solution of 5-bromo-pyridine-3-amine (100 mg, 0.57 mmol) and 3-cyclopentyloxy-4-methoxy-benzaldehyde (127 mg, 0.57 mmol) in 10 ml of 1,2-dichloroethtane (DCE), of HOAc (66 μL, 2 eq. 1.16 mmol) was added, the mixture was stirred overnight at room temperature, followed by addition of 15 ml of DCE. The organic phase was washed with water, and dried over sodium sulfate. The solvent was removed by under reduced pressure to give 200 mg of crude 5-bromo-N-(3-(cyclopentyloxy)-4-methoxybenzyl)pyridin-3-amine, which was used for the next step without further purification.

Source