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

HRID 2406722Notes

Reaction equation

HRID 2406722 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-57edb1d0dc704e7d998860e1003871d2
Source dataset
uspto-grants-2014_08
Patent number
US08809371B2

Reaction notes

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