Reaction #172026

Reaction equation

(R)-tert-butyl 1-(3-bromo-4-cyanophenylamino)-3-methoxypropan-2-ylcarbamate

5-amino-3-methylisothiazole hydrochloride

BINAP

K2CO3

→

(R)-tert-butyl 1-(4-cyano-3-(3-methylisothiazol-5-ylamino)phenylamino)-3-methoxypropan-2-ylcarbamate

Conditions

Workup

1. 1
   Otherwas degassed with Ar
2. 2
   Filtrationwas filtered
3. 3
   Filtrationfilter cake
4. 4
   Washwas washed with EtOAc
5. 5
   Concentrationthe filtrated was concentrated in vacuo

Procedure

A mixture of (R)-tert-butyl 1-(3-bromo-4-cyanophenylamino)-3-methoxypropan-2-ylcarbamate (150 mg, 0.39 mmol), 5-amino-3-methylisothiazole hydrochloride (76 mg, 0.51 mmol), BINAP (25 mg, 0.04 mmol), Pd(OAc)2 (18 mg, 0.08 mmol) and K2CO3 (188 mg, 1.37 mmol) p-dioxane (3 mL) was degassed with Ar, then was heated at 120° C. for 15 h. the mixture was filtered, filter cake was washed with EtOAc, and the filtrated was concentrated in vacuo to give (R)-tert-butyl 1-(4-cyano-3-(3-methylisothiazol-5-ylamino)phenylamino)-3-methoxypropan-2-ylcarbamate as crude oil.

Source