Lithium Hydroxide → 5-(2-Methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

HRID 2250442Notes

Reaction equation

HRID 2250442 reaction equation
C([O:3][C:4]([C:6]1[NH:19][C:9]2=[CH:10][N:11]=[C:12]([O:14][CH2:15][CH2:16][O:17][CH3:18])[CH:13]=[C:8]2[CH:7]=1)=[O:5])C.[Li+].[OH-]>C1COCC1.CO>[CH3:18][O:17][CH2:16][CH2:15][O:14][C:12]1[CH:13]=[C:8]2[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[NH:19][C:9]2=[CH:10][N:11]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59820057ethyl 5-(2-methoxyethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Product 1

HCID 692283985-(2-Methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1 g (3.784 mmol) 5-(2-Methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid ethyl ester (example 10 (iii)) in 50 mL THF and 25 mL MeOH 15.14 mL of a 1M LiOH solution were added. The mixture was stirred for 2 h at room temperature. The organic solvents were removed in vacuo, the solution acidified and concentrated in vacuo. The residue was purified by flash chromatography over silica gel using H2Cl2/MeOH/HOAc/H2O=90/10/1/1 as eluent. The product fractions were combined, concentrated in vacuo and lyophilized.

Workup

  1. customThe organic solvents were removed in vacuo
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography over silica gel
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34c9cf3d15c8491baf660a184dacdf04
Source dataset
uspto-grants-2008_01
Patent number
US07317027B2

Reaction notes

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