N-bromobutanimide → 6-Benzyloxy-5-bromo-3-fluoro-2-methoxy-pyridine

HRID 912625Notes

Reaction equation

HRID 912625 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]([O:15][CH3:16])[C:12]([F:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C(=O)N([Br:25])C(=O)C1>CN(C=O)C>[CH2:1]([O:8][C:9]1[N:14]=[C:13]([O:15][CH3:16])[C:12]([F:17])=[CH:11][C:10]=1[Br:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 671272546-Benzyloxy-3-fluoro-2-methoxy-pyridine

Product 1

HCID 671273216-Benzyloxy-5-bromo-3-fluoro-2-methoxy-pyridineYield 37.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

step 3—A solution 142 (1 g, 4.29 mmol) in DMF (10 mL) was cooled in ice-bath and NBS (0.763 g, 4.29 mmol) was added. The colorless mixture was stirred for 2 h and then quenched with H2O. The mixture was extracted with EtOAc (2×50 mL). The combined extracts were washed sequentially with H2O and brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography to afford 0.5 g of 6-benzyloxy-5-bromo-3-fluoro-2-methoxy-pyridine (144).

Workup

  1. customquenched with H2O
  2. extractionThe mixture was extracted with EtOAc (2×50 mL)
  3. washThe combined extracts were washed sequentially with H2O and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-f5728ce257cd448285b2c97269edc00e
Source dataset
uspto-grants-2011_09
Patent number
US08026253B2

Reaction notes

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