Reaction #172011

Reaction equation

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

5-amino-3-methylisothiazole hydrochloride

BINAP

K2CO3

→

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

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 brine
6. 6
   Dryingdried over Na2SO4
7. 7
   Concentrationconcentrated in vacuo

Procedure

A mixture of (R)-2-(3-bromo-4-cyanophenylamino)-2-phenylacetamide (78 mg, 0.236 mmol), 5-amino-3-methylisothiazole hydrochloride (47 mg, 0.312 mmol), BINAP (30 mg, 0.048 mmol), Pd(OAc)2 (20 mg, 0.089 mmol) and K2CO3 (134 mg, 0.971 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 brine, dried over Na2SO4, concentrated in vacuo to give (R)-2-(4-cyano-3-(3-methylisothiazol-5-ylamino)phenylamino)-2-phenylacetamide as a crude residue.

Source