Diethyl Ether → 7-bromo-3-chloro-5-vinyl-5H-chromeno[2,3-c]pyridin-5-ol

HRID 335980Notes

Reaction equation

HRID 335980 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1[CH:8]=[N:9][C:10]([Cl:12])=[CH:11][C:6]=1[C:5]2=[O:17].[CH:18]([Mg]Cl)=[CH2:19].CCOCC>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1[CH:8]=[N:9][C:10]([Cl:12])=[CH:11][C:6]=1[C:5]2([CH:18]=[CH2:19])[OH:17]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 574756367-Bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-oneHCID 178461836HCID 178461836, compound

Product 1

HCID 866585017-bromo-3-chloro-5-vinyl-5H-chromeno[2,3-c]pyridin-5-olYield 82.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-one (3.0 g, 9.66 mmol) at −78° C. in THF (48 mL) was added dropwise of vinylmagnesium chloride (17.51 mL, 28.0 mmol). After 30 min, the reaction was allowed to slowly warm to rt, then the reaction was quenched with 60 mL of saturated aqueious NH4Cl. The mixture was extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated in vacuo to yield 3.2 g of crude product as orange foam. This material was added ˜4 mL of Et2O and precipitate was formed and filtered through Bucher funnel to yield 7-bromo-3-chloro-5-vinyl-5H-chromeno[2,3-c]pyridin-5-ol (2.70 g, 7.97 mmol) as a yellow solid.

Workup

  1. customthe reaction was quenched with 60 mL of saturated aqueious NH4Cl
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto yield 3.2 g of crude product as orange foam
  7. customprecipitate was formed
  8. filtrationfiltered through Bucher funnel

Sources & evidence

ORD record
ord-169d415998b8472f9eb9cd35ff1386ca
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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