Reaction #172002

Reaction equation

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

5-amino-3-methylisothiazole hydrochloride

BINAP

K2CO3

→

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

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
   Dryingdried over Na2SO4
6. 6
   Concentrationconcentrated in vacuo

Procedure

A mixture of (R)-3-(benzyloxy)-2-(3-bromo-4-cyanophenylamino)propanamide (66 mg, 0.176 mmol), 5-amino-3-methylisothiazole hydrochloride (35 mg, 0.232 mmol), BINAP (20 mg, 0.032 mmol), Pd(OAc)2 (15 mg, 0.066 mmol) and K2CO3 (100 mg, 0.724 mmol) in dioxane (2 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, dried over Na2SO4, concentrated in vacuo to give (R)-3-(benzyloxy)-2-(4-cyano-3-(3-methylisothiazol-5-ylamino)phenylamino)propanamide as a crude residue (73 mg).

Source