Reaction #172001

Reaction equation

2-bromo-4-fluorobenzonitrile

O-benzyl-D-serinamide

DIEA

Water

→

(R)-3-(benzyloxy)-2-(3-bromo-4-cyanophenylamino)propanamide

Yield 17.6%

Solvents

DMSO

EtOAc

Conditions

Workup

1. 1
   OtherThe organic phase was separated
2. 2
   Washwashed with 1N HCl
3. 3
   Dryingdried over Na2SO4
4. 4
   Concentrationconcentrated in vacuo
5. 5
   OtherThe residue was purified by a silica gel column
6. 6
   Washeluted with 0-60% EtOAc in hexane

Procedure

A solution of 2-bromo-4-fluorobenzonitrile (200 mg, 1.00 mmol), O-benzyl-D-serinamide (290 mg, 1.49 mmol) and DIEA (0.466 mL, 2.68 mmol) in DMSO (3 mL) was stirred at 100 C for 18 h. Water and EtOAc were added. The organic phase was separated, washed with 1N HCl, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with 0-60% EtOAc in hexane to give (R)-3-(benzyloxy)-2-(3-bromo-4-cyanophenylamino)propanamide (66 mg).

Source