Reaction #171990

Reaction equation

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

5-amino-3-methylisothiazole hydrochloride

BINAP

K2CO3

→

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

Yield 61.1%

Solvents

dioxane

Conditions

Workup

1. 1
   Otherwas degassed with Ar
2. 2
   ConcentrationThe mixture was concentrated in vacuo
3. 3
   OtherThe residue was purified by HPLC

Procedure

A mixture of (R)-2-(3-bromo-4-cyanophenylamino)propanamide (185 mg, 0.690 mmol), 5-amino-3-methylisothiazole hydrochloride (133 mg, 0.883 mmol), BINAP (40 mg, 0.064 mmol), Pd(OAc)2 (30 mg, 0.13 mmol) and K2CO3 (300 mg, 2.17 mmol) in dioxane (4 mL) was degassed with Ar, then was stirred at 120 C for 18 h. The mixture was concentrated in vacuo. The residue was purified by HPLC to give ((R)-2-(4-cyano-3-(3-methylisothiazol-5-ylamino)phenylamino)propanamide (127 mg).

Source