Potassium Carbonate → HCID 44608069, compound

HRID 1943662Notes

Reaction equation

HRID 1943662 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10]([N:12]2[CH2:17][CH2:16][O:15][C:14]3[CH:18]=[CH:19][N:20]=[CH:21][C:13]2=3)=[O:11])[CH:5]=[C:6]([Br:9])[C:7]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].[C:28]([O:31][CH2:32]Br)(=[O:30])[CH3:29]>CN(C)C=O>[CH3:32][O:31][C:28](=[O:30])[CH2:29][O:8][C:7]1[C:6]([Br:9])=[CH:5][C:4]([C:10]([N:12]2[CH2:17][CH2:16][O:15][C:14]3[CH:18]=[CH:19][N:20]=[CH:21][C:13]2=3)=[O:11])=[CH:3][C:2]=1[Br:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68536Bromomethyl acetateHCID 44608229Epaminurad

Product 1

HCID 44608069HCID 44608069, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 25 ml flask, (3,5-dibromo-4-hydroxy-phenyl)-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanone (100 mg, 0.24 mmol) was dissolved in N,N-dimethyl formamide (2.4 ml), and potassium carbonate (37 mg, 0.266 mmol) was added thereto dropwise at room temperature. After stirring at room temperature for 10 minutes, bromo-methyl acetate was added dropwise and then stirred for 40 minutes at room temperature. The reaction mixture was filtered on celite and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of dichloromethane:methanol=20:1 to obtain the target compound 24 as white foam (48 mg, 41.0%).

Workup

  1. customdropwise at room temperature
  2. stirringstirred for 40 minutes at room temperature
  3. filtrationThe reaction mixture was filtered on celite
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica eluting with a solvent of dichloromethane

Sources & evidence

ORD record
ord-2bd173ac35f840e6aba3967ff1295a8c
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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