N-bromobutanimide → 5-Bromo-2,3-dihydro-7-azaindole

HRID 2080010Notes

Reaction equation

HRID 2080010 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH2:3][CH2:2]1.[Br:10]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Br:10][C:8]1[CH:9]=[C:4]2[CH2:3][CH2:2][NH:1][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 100118891H,2H,3H-pyrrolo(2,3-b)pyridine

Product 1

HCID 219640795-Bromo-2,3-dihydro-7-azaindoleYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine described in Preparation Example R-3 (15 mg, 0.13 mmol) and N-bromosuccinimide (24 mg, 0.14 mmol) were dissolved in N,N-dimethylformamide (0.5 mL), and the solution was stirred for 15 hours at room temperature. An aqueous solution of saturated sodium bicarbonate was added to the reaction solution at 0+ C., which was then extracted with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1), and the title compound (12 mg, 60 μmol, 48%) was obtained as a white solid.

Workup

  1. extraction, which was then extracted with ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-e2400e752fb34ec1b3fef49f4de9dc82
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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