Reaction #171999

Reaction equation

(R)-2-(3-bromo-4-cyanophenylamino)-3-phenylpropanamide

5-amino-3-methylisothiazole hydrochloride

BINAP

K2CO3

→

(R)-2-(4-cyano-3-(3-methylisothiazol-5-ylamino)phenylamino)-3-phenylpropanamide

Solvents

dioxane

Conditions

Workup

1. 1
   Otherwas degassed with Ar
2. 2
   workup.ADDITIONWater and EtOAc were added
3. 3
   FiltrationAfter being filtered
4. 4
   Otherthe organic phase was separated
5. 5
   Washwashed with 1N HCl
6. 6
   Dryingdried over Na2SO4
7. 7
   Concentrationconcentrated in vacuo

Procedure

A mixture of (R)-2-(3-bromo-4-cyanophenylamino)-3-phenylpropanamide (102 mg, 0.296 mmol), 5-amino-3-methylisothiazole hydrochloride (58 mg, 0.385 mmol), BINAP (25 mg, 0.040 mmol), Pd(OAc)2 (20 mg, 0.089 mmol) and K2CO3 (150 mg, 1.08 mmol) in dioxane (3 mL) was degassed with Ar, then was stirred at 120 C for 18 h. Water and EtOAc were added. After being filtered, the organic phase was separated, washed with 1N HCl, dried over Na2SO4, concentrated in vacuo to give (R)-2-(4-cyano-3-(3-methylisothiazol-5-ylamino)phenylamino)-3-phenylpropanamide as a crude residue.

Source