Sodium Hydroxide → 3-Phenyl-3-(1H-pyrrolo[2,3-c]pyridin-3-yl)-propionic acid

HRID 1869204Notes

Reaction equation

HRID 1869204 reaction equation
C([O:3][C:4](=[O:27])[CH:5]([CH:11]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:12]1[C:20]2[C:15](=[CH:16][N:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)C(OCC)=O)C.[OH-].[Na+]>CO>[C:21]1([CH:11]([C:12]2[C:20]3[C:15](=[CH:16][N:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH2:5][C:4]([OH:27])=[O:3])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57985922HCID 57985922, compound

Product 1

HCID 579858783-Phenyl-3-(1H-pyrrolo[2,3-c]pyridin-3-yl)-propionic acidYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a RT solution of 2-[phenyl-(1H-pyrrolo[2,3-c]pyridin-3-yl)-methyl]-malonic acid diethyl ester (0.33 g) in MeOH (30 mL) was added NaOH (2 M in water, 10 ml). The mixture was refluxed for 5h, cooled to RT, and concentrated. The residue was acidified by addition of HCl (1 M) and extracted with EtOAc. The combined extracts were refluxed for 10 h, cooled to RT, and concentrated. The residue was partitioned between water and EtOAc and extracted 3 times with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated, affording crude 3-Phenyl-3-(1H-pyrrolo[2,3-c]pyridin-3-yl)-propionic acid (224 mg, 94% yield), which was used in the next step without further purification.

Workup

  1. concentrationconcentrated
  2. additionThe residue was acidified by addition of HCl (1 M)
  3. extractionextracted with EtOAc
  4. temperatureThe combined extracts were refluxed for 10 h
  5. temperaturecooled to RT
  6. concentrationconcentrated
  7. customThe residue was partitioned between water and EtOAc
  8. extractionextracted 3 times with EtOAc
  9. dry with materialThe combined organic layers were dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-74eceeccb7b14ce1b0e9a4b91d8128ef
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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