Potassium Carbonate → HCID 72210907, compound

HRID 2209282Notes

Reaction equation

HRID 2209282 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([Br:9])[N:3]=1.C([O-])([O-])=O.[K+].[K+].Br[C:17]([CH3:24])([CH3:23])[C:18](OCC)=[O:19]>CC(C)=O>[Br:9][C:4]1[CH:5]=[CH:6][C:7]2[O:8][C:17]([CH3:24])([CH3:23])[C:18](=[O:19])[NH:1][C:2]=2[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 552649842-Amino-6-bromopyridin-3-ol

Product 1

HCID 72210907HCID 72210907, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 2-amino-6-bromopyridin-3-ol (250 mg, 1.32 mmol) and K2CO3 in acetone (5 mL) was added ethyl 2-bromoisobutyrate (0.29 ml, 1.98 mmol) and the reaction was stirred for 1 hour at room temperature and overnight at reflux. The acetone was removed, and to the residue was added dichloromethane and water. The layers were separated and the aqueous was extracted with dichloromethane (1x). The organic layer was dried (MgSO4), filtered, and concentrated to afford 6-bromo-2,2-dimethyl-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one 7.27 (300 mg). LCMS-ESI+ (m/z): [M+H]+ calcd for C9H10BrN2O2: 257.0; found: 257.1.

Workup

  1. temperatureat reflux
  2. customThe acetone was removed
  3. additionto the residue was added dichloromethane and water
  4. customThe layers were separated
  5. extractionthe aqueous was extracted with dichloromethane (1x)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1957d623ea1d4c8a9955e203eaf90de5
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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