N-bromobutanimide → HCID 178517583, compound

HRID 518477Notes

Reaction equation

HRID 518477 reaction equation
[Cl:1][C:2]1[O:11][C:5]2=[C:6]([OH:10])[N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1.C1C(=O)N([Br:19])C(=O)C1>CN(C=O)C>[Br:19][C:9]1[CH:8]=[N:7][C:6]([OH:10])=[C:5]2[O:11][C:2]([Cl:1])=[CH:3][C:4]=12

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178517667HCID 178517667, compound

Product 1

HCID 178517583HCID 178517583, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 0.15 M solution of 2-chlorofuro[2,3-c]pyridin-7-ol (113 mg, 0.7 mmol) in DMF stirred in the dark at 0° C. under an atmosphere of nitrogen was treated with NBS (120 mg, 0.7 mmol) in three equal portions. The ice bath was removed; the mixture was stirred at rt for 3 h. The reaction mixture was treated with a 10% aqueous solution of sodium thiosulfate (5 ml) and was extracted with EtOAc (3×30 mL). The combined organic layers were washed with water (15 mL), brine (20 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica gel (hexanes/EtOAc=4:1) to afford the title compound (145 mg, 87%) as a white solid. LCMS (M+H)+=249.

Workup

  1. customThe ice bath was removed
  2. additionThe reaction mixture was treated with a 10% aqueous solution of sodium thiosulfate (5 ml)
  3. extractionwas extracted with EtOAc (3×30 mL)
  4. washThe combined organic layers were washed with water (15 mL), brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel (hexanes/EtOAc=4:1)

Sources & evidence

ORD record
ord-d6d40f5ec85e4891aa8715e989191967
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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