6-Azaindole → HCID 57516335, compound

HRID 1810994Notes

Reaction equation

HRID 1810994 reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[H-].[Na+].[CH2:12]([O:19][C:20](=[O:23])[CH2:21]Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH4+].[Cl-]>CN(C=O)C>[CH2:12]([O:19][C:20](=[O:23])[CH2:21][N:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 92196-AzaindoleHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 62576Benzyl bromoacetate

Product 1

HCID 57516335HCID 57516335, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 1H-pyrrolo[2,3-c]pyridine (1 g, 8.46 mmol) in DMF (10 mL) under nitrogen atmosphere NaH (0.504 g, 12.6 mmol) is added in portions at ice-cold conditions. The reaction mixture is allowed to stir for 30 min at room temperature. It is then cooled in an ice-bath and bromoacetic acid benzyl ester (1.46 mL, 9.31 mmol) in DMF (10 mL) is added dropwise. The reaction mixture is stirred at room temperature for 5 h. Saturated aqueous NH4Cl solution is added to quench the reaction mixture at ice-cold conditions, then diluted with water (200 mL) and extracted with EtOAc (3×100 mL). Combined organic layer is washed with water followed by brine. It is then dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue is purified by column chromatography (silica-gel, 100-200 mesh, eluent; EtOAc to 2% MeOH in EtOAc) to afford pyrrolo[2,3-c]pyridin-1-yl-acetic acid benzyl ester (1.4 g) as a solid.

Workup

  1. temperatureIt is then cooled in an ice-bath
  2. stirringThe reaction mixture is stirred at room temperature for 5 h
  3. customto quench the reaction mixture at ice-cold conditions
  4. additiondiluted with water (200 mL)
  5. extractionextracted with EtOAc (3×100 mL)
  6. washCombined organic layer is washed with water
  7. dry with materialIt is then dried over anhydrous MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is purified by column chromatography (silica-gel, 100-200 mesh, eluent; EtOAc to 2% MeOH in EtOAc)

Sources & evidence

ORD record
ord-ee87548e1e5942f6bcce0e70da4f0397
Source dataset
uspto-grants-2013_01
Patent number
US08362249B2

Reaction notes

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