Reaction #172056

Reaction equation

2-bromo-4-(2-oxoazepan-3-ylamino)benzonitrile

5-amino-3-methylisothiazole hydrochloride

K2CO3

BINAP

→

2-(3-methylisothiazol-5-ylamino)-4-(2-oxoazepan-3-ylamino)benzonitrile

Yield 159.2%

Solvents

dioxane

Conditions

Workup

1. 1
   Otherwas degassed with argon
2. 2
   workup.ADDITIONWater and EtOAc were added
3. 3
   OtherThe organic phase was separated
4. 4
   Dryingdried over Na2SO4
5. 5
   Concentrationconcentrated in vacuo

Procedure

A mixture of 2-bromo-4-(2-oxoazepan-3-ylamino)benzonitrile (81 mg, 0.263 mmol), 5-amino-3-methylisothiazole hydrochloride (63 mg, 0.418 mmol), K2CO3 (120 mg, 0.869 mmol), BINAP (40 mg, 0.064 mmol) and Pd(OAc)2 (20 mg, 0.089 mmol) in dioxane (3 mL) was degassed with argon, then was stirred at 120 C for 18 h. Water and EtOAc were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo to give 2-(3-methylisothiazol-5-ylamino)-4-(2-oxoazepan-3-ylamino)benzonitrile (143 mg)

Source