Water → HCID 57985885, compound

HRID 1869190Notes

Reaction equation

HRID 1869190 reaction equation
C([O:3][C:4](=[O:29])[CH:5]([CH:11]([C:18]1[C:26]2[C:21](=[N:22][CH:23]=[CH:24][C:25]=2[O:27][CH3:28])[NH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([O:8]CC)=[O:7])C.O.[OH-].[K+]>C1COCC1.CCO>[CH3:28][O:27][C:25]1[CH:24]=[CH:23][N:22]=[C:21]2[NH:20][CH:19]=[C:18]([CH:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:5]([C:4]([OH:29])=[O:3])[C:6]([OH:8])=[O:7])[C:26]=12

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 57985925HCID 57985925, compound

Product 1

HCID 57985885HCID 57985885, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 2-[(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-phenyl-methyl]-malonic acid diethyl ester (1.0 g, 2.52 mmol) in a mixture of THF/EtOH (1/1, 24 ml) was added H2O (2 ml) followed by KOH (1.41 g, 25.2 mmol). The reaction mixture was stirred at 50° C. for 4 h, and then cooled to RT and concentrated. The solid residue was dissolved in H2O. The resulting solution was cooled to 0° C. and acidified to pH 4-5 by addition of HCl (I M). The white solid precipitate was collected by filtration, washed with cold H2O and dried to afford 2-[(4-Methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-phenyl-methyl]-malonic acid (809 mg, 94% yield).

Workup

  1. temperaturecooled to RT
  2. concentrationconcentrated
  3. dissolutionThe solid residue was dissolved in H2O
  4. temperatureThe resulting solution was cooled to 0° C.
  5. additionacidified to pH 4-5 by addition of HCl (I M)
  6. filtrationThe white solid precipitate was collected by filtration
  7. washwashed with cold H2O
  8. customdried

Sources & evidence

ORD record
ord-d319352e808e41a79660c457f9ad0e61
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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