Sodium Iodide → 4-Iodo-1-acetyl-7-azaindole

HRID 887645Notes

Reaction equation

HRID 887645 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[Na+].[I-:12].[C:13](Cl)(=[O:15])[CH3:14].C([O-])([O-])=O.[Na+].[Na+].OS([O-])=O.[Na+]>CC#N>[I:12][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([C:13](=[O:15])[CH3:14])[CH:9]=[CH:10][C:3]=12

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 6367Acetyl chlorideHCID 10340Sodium CarbonateHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 23665763Sodium Bisulfite

Product 1

HCID 112661324-Iodo-1-acetyl-7-azaindole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 4-chloro-1H-pyrrolo[2,3-b]pyridine (3.80 g, step B) and NaI (19.15 g) in CH3CN (40 mL) was added acetyl chloride (5.0 mL) slowly. The mixture was heated to reflux for overnight. After cooled to RT, 40 mL of 10% Na2CO3 and 40 mL of 10% NaHSO3 were added. After stirring for 15 min, the mixture was extracted with EtOAc 4 times. The combined organic phases were washed with brine, dried over MgSO4 and concentrated to give a brown residue as the crude compound, which was purified by chromatography through silica gel (220 g, 5 to 15% EtOAc/hexanes to afford 1-(4-iodo-pyrrolo[2,3-b]pyridin-1-yl)-ethanone as white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for overnight
  3. extractionthe mixture was extracted with EtOAc 4 times
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give a brown residue as the crude compound, which
  8. customwas purified by chromatography through silica gel (220 g, 5 to 15% EtOAc/hexanes

Sources & evidence

ORD record
ord-bef1992222d64097a2e6b055cc9e86fb
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

Loading…