Water → 1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile

4-Chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (2.84 g, 9.2 mmol), zinc cyanide (650 mg, 5.5 mmol), and zinc dust (120 mg, 1.8 mmol) were suspended in dimethylacetamide (40 mL). The mixture was degassed thoroughly, bis(tri-t-butylphosphine)palladium (511 mg, 0.46 mmol) was added, and the mixture was stirred at 80° C. for 3d. The mixture was poured into water (80 mL) and filtered. The solids were washed with ethyl acetate and the filtrates were combined. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and concentrated. The oily residue was triturated with hexanes, the solution was decanted and the solvent was evaporated to give 1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile (676 mg, 2.25 mmol, 25% yield).

1. customThe mixture was degassed thoroughly
2. filtrationfiltered
3. washThe solids were washed with ethyl acetate
4. customThe organic layer was separated
5. washwashed with water and brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated
8. customThe oily residue was triturated with hexanes
9. customthe solution was decanted
10. customthe solvent was evaporated

ORD record

ord-055a418d2b2243a4a0e278ec355cb396

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158647B2