Reacción #69137

Ecuación de reacción

2-(methylsulfonyl)-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile

benzenethiol

DIPEA

LiOH.H2O

→

title compound

Rendimiento 47.0%

2-(phenylthio)-4-(5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile

Rendimiento 47.0%

Disolventes

THF

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITthe reaction left
2. 2
   OtroThe reaction was partitioned between EtOAc and water
3. 3
   Extracciónthe aqueous phase extracted with EtOAc
4. 4
   SecadoThe combined organic layers were dried (Na2SO4)
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe resultant solid was purified by column chromatography (ISCO Companion™, 12 g column, 0-30% EtOAc/Petroleum Ether)

Procedimiento

2-(methylsulfonyl)-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile (75 mg, 0.15 mmol) was heated with benzenethiol (31 uL, 0.30 mmol, 2.0 Eq.) and DIPEA (78 uL, 0.45 mmol, 3.0 Eq.) in THF (2 mL) under microwave conditions at 100° C. for 10 minutes. A solution of LiOH.H2O (32 mg, 0.75 mmol, 5.0 Eq.) in water (1 mL) was added to the mixture and the reaction left to stir for 90 minutes. The reaction was partitioned between EtOAc and water and the aqueous phase extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The resultant solid was purified by column chromatography (ISCO Companion™, 12 g column, 0-30% EtOAc/Petroleum Ether) and lyophilized to give the title compound as a pale yellow solid (28 mg, 47% over 2 steps).

Fuente