Bromine → 5-Bromo-4-(trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridine

HRID 2389895Notes

Reaction equation

HRID 2389895 reaction equation
[CH3:1][Si:2]([CH3:13])([CH3:12])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[O:9][CH2:10][CH2:11][C:4]=12.C(=O)([O-])O.[Na+].[Br:19]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[Br:19][C:8]1[C:3]([Si:2]([CH3:13])([CH3:12])[CH3:1])=[C:4]2[CH2:11][CH2:10][O:9][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 591794274-(Trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridine

Product 1

HCID 591794545-Bromo-4-(trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridineYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridine (463 mg, 2.40 mmol) in dichloromethane (10 mL) were added sodium hydrogen carbonate (504 mg, 6.00 mmol) and bromine (959 mg, 6.00 mmol) at room temperature, and the mixture was stirred for 9 hr. An aqueous sodium thiosulfate solution was added to the reaction solution, and the mixture was extracted with dichloromethane. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95→30/70) to give the title compound (522 mg, yield 80%).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95→30/70)

Sources & evidence

ORD record
ord-e41a872f487949ac99beb311eb59dcfb
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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