Benzyl Bromide → 1-Benzyl-3-bromo-1H-pyrrolo[2,3-b]pyridine

HRID 1778880Notes

Reaction equation

HRID 1778880 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].Br[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O>[CH2:14]([N:4]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:10]2[C:2]([Br:1])=[CH:3]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 55236593-Bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 154556171-Benzyl-3-bromo-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromo-1H-pyrrolo[2,3-b]pyridine (500 mg) in N,N-dimethylformamide (10 mL) was added NaH (70 mg). The mixture was stirred for 50 minutes, and (bromomethyl)benzene (0.290 mL) was added dropwise. The reaction was stirred for 48 hours and quenched by the addition of water and ethyl acetate. The layers were separated, and the organic layer was washed with brine, dried with Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography, eluting with 2:1 hexane to ethyl acetate, to give the title compound.

Workup

  1. stirringThe reaction was stirred for 48 hours
  2. customquenched by the addition of water and ethyl acetate
  3. customThe layers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with 2:1 hexane to ethyl acetate

Sources & evidence

ORD record
ord-18dc9a71d058467bb2bc438d2beeebc1
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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