HCID 57516335, compound → HCID 57516334, compound

HRID 1810995Notes

Reaction equation

HRID 1810995 reaction equation
C([O:8][C:9](=[O:20])[CH2:10][N:11]1[C:15]2=[CH:16][N:17]=[CH:18][CH:19]=[C:14]2[CH:13]=[CH:12]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[N:11]1([CH2:10][C:9]([OH:20])=[O:8])[C:15]2=[CH:16][N:17]=[CH:18][CH:19]=[C:14]2[CH:13]=[CH:12]1

Participants

5

Reactant 2

HCID 57516335HCID 57516335, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 57516334HCID 57516334, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of pyrrolo[2,3-c]pyridin-1-yl-acetic acid benzyl ester (1.0 g, 3.6 mmol) in MeOH (20 mL) in a Parr shaker vessel (250 mL), palladium-charcoal (100 mg) is added under nitrogen atmosphere. Nitrogen is flashed with hydrogen and the solution is hydrogenated at room temperature at 10 psi hydrogen pressure. Reaction is monitored by TLC. After complete consumption of starting material, the reaction mixture is taken out from the Parr shaker and diluted with water. The solution is filtered through a pad of diatomaceous earth and washed successively with hot water. Volatiles are removed under reduced pressure and crude solid obtained is washed with EtOAc (3×50 mL). It is concentrated and dried in vacuum to yield pyrrolo[2,3-c]pyridin-1-yl-acetic acid as a solid (0.565 g).

Workup

  1. customReaction
  2. customAfter complete consumption of starting material
  3. additiondiluted with water
  4. filtrationThe solution is filtered through a pad of diatomaceous earth
  5. washwashed successively with hot water
  6. customVolatiles are removed under reduced pressure
  7. customcrude solid obtained
  8. washis washed with EtOAc (3×50 mL)
  9. concentrationIt is concentrated
  10. customdried in vacuum

Sources & evidence

ORD record
ord-1fea5617912743d781faadb41cfe0dee
Source dataset
uspto-grants-2013_01
Patent number
US08362249B2

Reaction notes

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