Water → 2-(1H-pyrrolo[3,2-b]pyridin-3-yl)acetonitrile

HRID 731587Notes

Reaction equation

HRID 731587 reaction equation
CN(C)[CH2:3][C:4]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[NH:6][CH:5]=1.O.[C-:15]#[N:16].[Na+]>C1COCC1>[NH:6]1[C:7]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[C:4]([CH2:3][C:15]#[N:16])=[CH:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 12146847N,N-Dimethyl-1H-pyrrolo[3,2-b]pyridine-3-methanamine

Product 1

HCID 121468482-(1H-pyrrolo[3,2-b]pyridin-3-yl)acetonitrileYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of dimethyl-(1H-pyrrolo[3,2-b]pyridin-3-yl)methylamine (0.828 g, 4.73 mmol) in dry THF (20 mL) under nitrogen is treated with a solution of (CH3O)2SO2 (0.49 mL) in THF, heated at reflux temperature for 0.5 h, cooled in an ice bath, and decanted. The gummy residue is washed with ether, treated with water (15 mL) and NaCN (0.39 g, 6.2 mmol), heated at reflux temperature for 0.75 h, cooled and extracted with 4:1 CH2Cl2:ethanol. The combined extracts are dried over MgSO4 and concentrated in vacuo. The resultant residue is chromatographed (silica gel, ethyl acetate as eluent) to afford the title compound as a white solid, 0.51 g (68% yield), mp 201-202° C., identified by NMR and mass spectral analyses.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 0.5 h
  3. temperaturecooled in an ice bath
  4. customdecanted
  5. washThe gummy residue is washed with ether
  6. temperatureheated
  7. temperatureat reflux temperature for 0.75 h
  8. temperaturecooled
  9. extractionextracted with 4:1 CH2Cl2
  10. dry with materialThe combined extracts are dried over MgSO4
  11. concentrationconcentrated in vacuo
  12. customThe resultant residue is chromatographed (silica gel, ethyl acetate as eluent)

Sources & evidence

ORD record
ord-93deb04dd6af4019a5ae3674cab97067
Source dataset
uspto-grants-2009_09
Patent number
US07585876B2

Reaction notes

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