1-Hydroxy-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid ethyl ester → Ethyl 6-methyl-1H-pyrrolo[3,2-B]pyridine-3-carboxylate

HRID 1838306Notes

Reaction equation

HRID 1838306 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]2=[N:11][CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]2[N:8](O)[CH:7]=1)=[O:5])[CH3:2]>C(O)C.[OH-].[OH-].[Pd+2]>[CH2:1]([O:3][C:4]([C:6]1[C:10]2=[N:11][CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]2[NH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 600601751-Hydroxy-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid ethyl ester

Product 1

HCID 60060164Ethyl 6-methyl-1H-pyrrolo[3,2-B]pyridine-3-carboxylateYield 53.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Pd(OH)2 (200 mg) is added to a solution of 1-Hydroxy-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid ethyl ester (1.2 g, 0.005 mole) in ethanol (20 mL) and is hydrogenated at 50 psi for 24 h. The catalyst is removed by filtration through a pad of celite and the solvent evaporated under vacuum. The residue is chromatographed over silica gel eluting with 5% MeOH-DCM containing few drops of NH4OH to afford 6-Methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid ethyl ester (550 mg, 50%); 1H NMR (300 MHz, DMSO-d6) δ 1.28 (t, J=6 Hz, 3H), 2.38 (s, 3H), 4.24 (q, J=6.6 Hz, 2H), 7.62 (s, 1H); 8.17 (s, 1H), 8.31 (s, 1H); LRMS Calcd 204.23; found 205.15.

Workup

  1. customThe catalyst is removed by filtration through a pad of celite
  2. customthe solvent evaporated under vacuum
  3. customThe residue is chromatographed over silica gel eluting with 5% MeOH-DCM containing few drops of NH4OH

Sources & evidence

ORD record
ord-1b991254972b4a4c8bfe345e32471d94
Source dataset
uspto-grants-2004_01
Patent number
US06673811B1

Reaction notes

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