(4-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)methanol → 4-methoxy-2-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 1445922Notes

Reaction equation

HRID 1445922 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:9][C:10]([CH2:12]O)=[CH:11][C:4]=12>CO.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:9][C:10]([CH3:12])=[CH:11][C:4]=12

Participants

4

Reactant 1

HCID 15885418(4-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)methanol

Product 1

HCID 117884674-methoxy-2-methyl-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A suspension of (4-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)methanol 4 (0.90 g, 5.05 mmol) and Pd(OH)2 (100 mg) in methanol containing 4N aq. HCl solution (10 mL) was hydrogenated under hydrogen pressure (50 psi) for 36 h. The acidic mixture was quenched with 1N NaOH solution. Filtration through celite, concentration and purification on silica gel column using 5% methanol in CH2Cl2 to gave 5 as pale yellow syrup. Yield: 0.68 g, 83%; ESI MS: m/z 163.01 (M+1).

Workup

  1. customfor 36 h
  2. customThe acidic mixture was quenched with 1N NaOH solution
  3. filtrationFiltration
  4. concentrationthrough celite, concentration and purification on silica gel column

Sources & evidence

ORD record
ord-5264f5d2b0c04993aad992605ec1dbed
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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