Reacción #88589

Ecuación de reacción

(S)-4-(3-aminopyrrolidin-1-yl)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile

2,2,2-trifluoroethyl trifluoromethanesulfonate

N,N-diisopropylethylamine

→

title compound

(S)-4-(3-(2,2,2-trifluoroethylamino)pyrrolidin-1-yl)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile

Disolventes

water

methylene chloride

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe cooled reaction mixture
2. 2
   OtroThe organic layer was separated
3. 3
   Secadodried over sodium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   Otropurified by flash chromatography (silica, 4 g, ISCO, 0-20% methanol in methylene chloride)

Procedimiento

A mixture of (S)-4-(3-aminopyrrolidin-1-yl)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (131 mg, 0.32 mmol), 2,2,2-trifluoroethyl trifluoromethanesulfonate (490 mg, 2.1 mmol), and N,N-diisopropylethylamine (365 uL, 2.1 mmol) in methylene chloride (15 mL) was heated at 40° C. for 4 hours. The cooled reaction mixture was diluted with water (20 mL) and methylene chloride (50 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified by flash chromatography (silica, 4 g, ISCO, 0-20% methanol in methylene chloride) to afford the title compound as an oil, which was used in the next step without any further purification (156 mg, 100%).

Fuente