Benzyl Bromide → HCID 67374380, compound

HRID 1253551Notes

Reaction equation

HRID 1253551 reaction equation
[Br:1][C:2]1[C:3]2[N:4]([N:9]=[CH:10][CH:11]=2)[CH:5]=[C:6]([OH:8])[CH:7]=1.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C>[CH2:14]([O:8][C:6]1[CH:7]=[C:2]([Br:1])[C:3]2[N:4]([N:9]=[CH:10][CH:11]=2)[CH:5]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 67373747HCID 67373747, compound

Product 1

HCID 67374380HCID 67374380, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-bromopyrazolo[1,5-a]pyridin-6-ol (50.0 mg, 0.235 mmol) was dissolved in DMF (2 ml). NaH (14.1 mg, 0.352 mmol, 60%) was added in one portion, and the mixture was allowed to stir for 10 minutes. Benzyl bromide (0.031 ml, 0.258 mmol) was added and the mixture was allowed to stir for 30 minutes. The reaction mixture was quenched with saturated aqueous ammonium chloride, diluted in ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and brine then dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/isohexane gradient) to afford 6-(benzyloxy)-4-bromopyrazolo[1,5-a]pyridine.

Workup

  1. stirringto stir for 30 minutes
  2. customThe reaction mixture was quenched with saturated aqueous ammonium chloride
  3. additiondiluted in ethyl acetate
  4. washwashed with saturated aqueous sodium hydrogen carbonate and brine
  5. dry with materialthen dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (ethyl acetate/isohexane gradient)

Sources & evidence

ORD record
ord-7f3d2437e8114bd19960af1e239e490a
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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