Dibromomethane → 5-Bromo-[1,3]dioxolo[4,5-b]pyridine

HRID 1620074Notes

Reaction equation

HRID 1620074 reaction equation
Br[CH2:2][Br:3].[C:4](=[O:7])([O-])[O-:5].[Cs+].[Cs+].CN(C=O)C.Br[C:16]1[CH:17]=[C:18](O)[C:19](O)=[N:20]C=1>O>[Br:3][C:2]1[N:20]=[C:19]2[O:5][CH2:4][O:7][C:18]2=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 3024DibromomethaneHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 178515448HCID 178515448, compound

Product 1

HCID 823972135-Bromo-[1,3]dioxolo[4,5-b]pyridineYield 13.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dibromomethane (91 mg) and cesium carbonate (380 mg) were added to a tube containing a DMF (4 ml) solution containing 5-bromopyridin-2,3-diol (100 mg) and the tube was sealed, followed by stirring at 100° C.-110° C. for 8 hours. The reaction solution was adjusted to room temperature, and water was added, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=50:1 to 4:1), and a brown solid of 5-bromo-[1,3]dioxolo[4,5-b]pyridine (13.8 mg) was thus obtained.

Workup

  1. customthe tube was sealed
  2. customwas adjusted to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe resultant was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationSubsequently, the solvent was distilled away under reduced pressure
  7. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=50:1 to 4:1)

Sources & evidence

ORD record
ord-5a9f85048b6842808606f2d4bf703058
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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