Azobisisobutyronitrile → 5-(Bromomethyl)furo[3,2-b]pyridine

HRID 1492411Notes

Reaction equation

HRID 1492411 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[CH:8]=[CH:9][O:10][C:5]2=[CH:4][CH:3]=1.CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N([Br:30])C(=O)C1>>[Br:30][CH2:1][C:2]1[N:7]=[C:6]2[CH:8]=[CH:9][O:10][C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimide2×HCID 122102195-Methylfuro[3,2-b]pyridine

Product 1

HCID 189505795-(Bromomethyl)furo[3,2-b]pyridine

Conditions

Temperature
75 °C

Procedure

To a solution of 1.46 g (11.0 mmol) of 5-methylfuro[3,2b]pyridine (from Step 2) and 100 mg AIBN in 35 mL of CC14 was added 2.1 g (11.6 mmol) of NBS. The mixture was stirred at 75° C. under radiation from a 150 W spot light for 1 hr. Another portion of NBS was added (1.0 g) and the reaction was allowed to proceed for another 1.5 hr. The reaction was allowed to cool to r.t., diluted with aqueous NH4OAc 25% w/v (150 mL) and the mixture was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The resulting residue was purified by chromatography on silica gel eluted with 20-25 % EtOAc in hexane to give the title compound as a colorless oil.

Workup

  1. waitto proceed for another 1.5 hr
  2. temperatureto cool to r.t.
  3. extractionthe mixture was extracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe resulting residue was purified by chromatography on silica gel
  7. washeluted with 20-25 % EtOAc in hexane

Sources & evidence

ORD record
ord-2000c69cc5214cf7ac028f1b983b966e
Source dataset
uspto-grants-1994_12
Patent number
US05374635

Reaction notes

Loading…