N-bromobutanimide → 2-Acetyl-4-bromo-7-methoxyfuro[2,3-c]pyridine

HRID 564721Notes

Reaction equation

HRID 564721 reaction equation
[C:1]([C:4]1[O:14][C:7]2=[C:8]([O:12][CH3:13])[N:9]=[CH:10][CH:11]=[C:6]2[CH:5]=1)(=[O:3])[CH3:2].[Br:15]N1C(=O)CCC1=O>C(#N)C>[C:1]([C:4]1[O:14][C:7]2=[C:8]([O:12][CH3:13])[N:9]=[CH:10][C:11]([Br:15])=[C:6]2[CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 221127862-Acetyl-7-methoxyfuro[2,3-c]pyridine

Product 1

HCID 221127982-Acetyl-4-bromo-7-methoxyfuro[2,3-c]pyridineYield 92.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-acetyl-7-methoxyfuro[2,3-c]pyridine (1.1 g) in acetonitrile (50 ml) was stirred at room temperature. N-Bromosuccinimide (1.0 g) was added and stirring continued overnight. The reaction was quenched by the addition of water (50 ml) and extracted with dichloromethane (3×50 ml). The combined organic extracts were washed with water (50 ml), dried over magnesium sulfate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 33% ethyl acetate in hexane gave the title compound (1.4 g) as a white solid.

Workup

  1. customThe reaction was quenched by the addition of water (50 ml)
  2. extractionextracted with dichloromethane (3×50 ml)
  3. washThe combined organic extracts were washed with water (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customPurification by column chromatography on silica eluting with 33% ethyl acetate in hexane

Sources & evidence

ORD record
ord-2e7c30418e8d4b3780e455537f5dc0f4
Source dataset
uspto-grants-2001_01
Patent number
US06169090A

Reaction notes

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