Reaction #88559

Reaction equation

4-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile

3-methylpiperidin-3-ol

sodium hydride

→

title compound

(3-methylpiperidin-3-yloxy)-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile

Solvents

water

ethyl acetate

tetrahydrofuran

Conditions

Workup

1. 1
   workup.ADDITIONwas added in one portion
2. 2
   OtherThe organic layer was separated
3. 3
   Dryingdried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo
6. 6
   Otherpurified flash chromatography (silica, 40 g, ISCO, 1-20% methanol in methylene chloride)

Procedure

To a solution of 3-methylpiperidin-3-ol (99 mg, 0.86 mmol) in tetrahydrofuran (3.2 mL) was added sodium hydride as 60% dispersion in mineral oil (35 mg, 0.86 mmol). The reaction mixture was stirred at ambient temperature for 5 minutes before 4-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (141 mg, 0.39 mmol) was added in one portion and the reaction mixture was stirred at this temperature for 10 minutes before being warmed to 40° C. for 5 hours. The mixture was diluted with water (20 mL) and ethyl acetate (50 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified flash chromatography (silica, 40 g, ISCO, 1-20% methanol in methylene chloride) to afford the title compound as an orange solid, which was used in the next step without any further purification (52 mg, 30%).

Source