Water → HCID 71666040, compound

HRID 1507444Notes

Reaction equation

HRID 1507444 reaction equation
[Br:1]N1C(=O)CCC1=O.C([O:12][C:13]1[CH:22]=[C:21]2[C:16]([C:17](=[O:34])[C:18]([CH3:33])=[C:19]([CH:23]3[CH2:28][CH2:27][N:26]([C:29](=[O:32])[CH2:30][CH3:31])[CH2:25][CH2:24]3)[O:20]2)=[CH:15][CH:14]=1)C=C.O>CN(C)C=O>[Br:1][C:22]1[C:13]([OH:12])=[CH:14][CH:15]=[C:16]2[C:21]=1[O:20][C:19]([CH:23]1[CH2:28][CH2:27][N:26]([C:29](=[O:32])[CH2:30][CH3:31])[CH2:25][CH2:24]1)=[C:18]([CH3:33])[C:17]2=[O:34]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 117701775HCID 117701775, compound

Product 1

HCID 71666040HCID 71666040, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Bromosuccinimide (171 mg, 0.96 mmol) was added to a solution of 7-hydroxy-3-methyl-2-(1-propanoylpiperidin-4-yl)-4H-chromen-4-one (304 mg, 0.96 mmol) obtained in Example 31-3 in N,N-dimethylformamide (5 mL), and the mixture was stirred at room temperature for 5 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane/methanol=98/2→67/33) to obtain 204 mg of the title compound (yield: 54%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (dichloromethane/methanol=98/2→67/33)

Sources & evidence

ORD record
ord-f3bf4c998e2745f7b34d8465068d0b11
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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