Reaction #2358554

Reaction equation

water

sodium triacetoxyborohydride

5-bromopyridin-3-ylamine

material 1

5-bromopyridin-3-ylamine

2-hydroxybenzaldehyde

material 2

2-hydroxybenzaldehyde

→

2-[(5-Bromopyridin-3-ylamino)methyl]phenol

Solvents

dichloromethane

Conditions

Workup

1. 1
   workup.STIRRINGstirred for 2 h
2. 2
   ExtractionThe aqueous phase is extracted with dichloromethane
3. 3
   Washwashed with water
4. 4
   Dryingdried over sodium sulphate
5. 5
   OtherThe residue is chromatographed on silica gel (80/20 heptane/ethyl acetate)

Procedure

295 mg (1.4 mmol, 1.4 eq) of sodium triacetoxyborohydride are added to a solution of 173 mg (1 mmol, 1 eq) of 5-bromopyridin-3-ylamine (starting material 1) and 122 mg (1 mmol, 1 eq) of 2-hydroxybenzaldehyde (starting material 2) in 20 ml of dichloromethane. The solution is stirred at room temperature for 24 h. The medium is poured into water and stirred for 2 h. The aqueous phase is extracted with dichloromethane. The organic phases are combined, washed with water, and then dried over sodium sulphate. The residue is chromatographed on silica gel (80/20 heptane/ethyl acetate). 2-[(5-Bromopyridin-3-ylamino)methyl]phenol is obtained in the form of a white solid.

Source