3-Dimethylamino-2-(5-methyl-3-nitro-pyridin-2-yl)-acrylic acid ethyl ester → 1-Hydroxy-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid ethyl ester

HRID 1838305Notes

Reaction equation

HRID 1838305 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]([C:10]1[C:15]([N+:16]([O-])=[O:17])=[CH:14][C:13]([CH3:19])=[CH:12][N:11]=1)=[CH:6]N(C)C)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:5]1[C:10]2=[N:11][CH:12]=[C:13]([CH3:19])[CH:14]=[C:15]2[N:16]([OH:17])[CH:6]=1)=[O:20])[CH3:2]

Participants

4

Reactant 1

HCID 698499683-Dimethylamino-2-(5-methyl-3-nitro-pyridin-2-yl)-acrylic acid ethyl ester

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-Dimethylamino-2-(5-methyl-3-nitro-pyridin-2-yl]-acrylic acid ethyl ester (6.2 g, 0.022 mol) in ethanol (50 mL) is hydrogenated over 10% Pd-C at 50 psi for 48 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 7% MeOH-DCM containing few drops of NH4OH to afford 1-Hydroxy-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid ethyl ester 1H NMR (300 MHz, DMSO-d6) δ 1.25 (t, J=6.6 Hz, 3H), 4.21 (q, J=6.6 Hz, 2H), 7.59 (s, 1H), 8.15 (s, 1H), 8.29 (s, 1H); LRMS Calcd 220.2; found 221.12.

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 7% MeOH-DCM containing few drops of NH4OH

Sources & evidence

ORD record
ord-e5a8858b78d843e79beae1c2b3ddaf8f
Source dataset
uspto-grants-2004_01
Patent number
US06673811B1

Reaction notes

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