Bromine → HCID 13849603, compound

HRID 580294Notes

Reaction equation

HRID 580294 reaction equation
C([O-])(=O)C.[Na+].[Br:6]Br.[Br:8][C:9]1[C:17]2[C:12](=[N:13][C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:16]=2)[O:11][CH:10]=1.N12CCCN=C1CCCCC2>C(Cl)Cl>[Br:6][C:10]1[O:11][C:12]2=[N:13][C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:16]=[C:17]2[C:9]=1[Br:8]

Participants

6

Reactant 4

HCID 24408BromineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 517045Sodium AcetateHCID 13849602HCID 13849602, compound

Product 1

HCID 13849603HCID 13849603, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium acetate (2.40 g, 0.0292 mol) and bromine (7.5 mL, 0.146 mol) are added to a solution of diethyl 3-bromofuro[2,3-b]pyridine-5,6-dicarboxylate (5.00 g, 0.0146 mol) in methylene chloride (150 mL). The mixture is stirred at room temperature for four days then washed with aqueous sodium bisulfate to remove unreacted bromine. The aqueous solution is then back extracted with methylene chloride. The organic solution is combined, dried over sodium sulfate and filtered. To the filtrate is added 1,8-diazabicyclo[5.4.0]undec-7-ene(4.4 mL, 0.032 mol), and the mixture is stirred at room temperature for one hour. The solution is then concentrated in vacuo. The residue is chromatographed over silica gel eluting with 20% ethyl acetate in hexane, yielding the crude 2,3-dibromofuro[2,3-b]pyridine as a white solid in 95% yields recrystallization from a methylene chloride-hexane mixture affords diethyl 2,3-dibromofuro[2,3-b]pyridine-5,6-dicarboxylate mp 96°-98° C. in 75.9% recrystallized yield.

Workup

  1. washthen washed with aqueous sodium bisulfate
  2. customto remove unreacted bromine
  3. extractionThe aqueous solution is then back extracted with methylene chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. stirringthe mixture is stirred at room temperature for one hour
  7. concentrationThe solution is then concentrated in vacuo
  8. customThe residue is chromatographed over silica gel eluting with 20% ethyl acetate in hexane
  9. customyielding the crude 2,3-dibromofuro[2,3-b]pyridine as a white solid in 95%
  10. customyields
  11. customrecrystallization from a methylene chloride-hexane mixture

Sources & evidence

ORD record
ord-67dcbdd89bb94cbbb8d6fb3c2c8515d3
Source dataset
uspto-grants-1988_06
Patent number
US04752323

Reaction notes

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