Sodium Bicarbonate → HCID 67371976, compound

HRID 1678114Notes

Reaction equation

HRID 1678114 reaction equation
Br[C:2]1(Br)[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[C:3]1=[O:17].C(=O)([O-])O.[Na+]>[Pd].C(O)C>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([N:4]2[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:10]3[CH2:2][C:3]2=[O:17])[CH:12]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 67371016HCID 67371016, compound

Product 1

HCID 67371976HCID 67371976, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3,3-dibromo-1-pyridin-3-yl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (crude, 2.12 g) and 10% by weight palladium on activated charcoal (750 mg) are suspended in absolute ethanol (85 mL). This mixture is allowed to stir under a hydrogen atmosphere at atmospheric pressure for 19 hours. The reaction mixture is filtered through a pad of hyflo, washing the cake well with copious amounts of boiling ethanol. Concentration of the filtrate gives crude 1-pyridin-3-yl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one as an sticky brown solid. Saturated aqueous sodium hydrogen carbonate (30 mL) is added and the mixture extracted with 8 portions of dichloromethane. The combined extracts are dried over magnesium sulfate, filtered and evaporated to give a brown residue. The crude material is purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:methanol (99:1). Fractions containing the product are combined and evaporated to give 380 mg of 1-pyridin-3-yl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (47% yield starting from 3-bromopyridine). MS: m/e 212 (M+H). 1H NMR (300 MHz, CDCl3): 8.90 (1H, d), 8.62 (1H, dd), 8.19 (1H, d), 7.96 (1H, dt), 7.61 (1H, d), 7.47 (1H, dd), 7.08 (1H, dd), 3.78 (2H, s).

Workup

  1. filtrationThe reaction mixture is filtered through a pad of hyflo
  2. washwashing the cake well with copious amounts of boiling ethanol
  3. customConcentration of the filtrate gives crude 1-pyridin-3-yl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one as an sticky brown solid
  4. extractionthe mixture extracted with 8 portions of dichloromethane
  5. dry with materialThe combined extracts are dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give a brown residue
  9. customThe crude material is purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:methanol (99:1)
  10. additionFractions containing the product
  11. customevaporated

Sources & evidence

ORD record
ord-13a51a3204b04dbeb75ebc8c7665e26c
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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