Water → 1-[Tri(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile

HRID 1693698Notes

Reaction equation

HRID 1693698 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:10][C:3]=12.O.C[C:23]([N:25](C)C)=O>[C-]#N.[Zn+2].[C-]#N.[Zn].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH:18]([Si:11]([CH:15]([CH3:16])[CH3:17])([CH:12]([CH3:13])[CH3:14])[N:8]1[C:4]2[N:5]=[CH:6][CH:7]=[C:2]([C:23]#[N:25])[C:3]=2[CH:10]=[CH:9]1)([CH3:19])[CH3:20]

Participants

7

Reactant 3

HCID 962WaterHCID 31374DimethylacetamideHCID 114382724-Chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 534382901-[Tri(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine-4-carbonitrileYield 25%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 178418851HCID 178418851, compoundCatalyst

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-055a418d2b2243a4a0e278ec355cb396
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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