Water → HCID 57855771, compound

HRID 475581Notes

Reaction equation

HRID 475581 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:10]2[O:11][CH:12]=[C:13]([CH2:15][CH2:16][C:17]([C:19]3[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=3)=[O:18])[N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].N12CCCN=C1CC[CH2:29][CH2:28][CH2:27]2.C(Br)C=C.O>C(O)C.C(OCC)(=O)C>[CH2:29]([O:1][C:2]1[CH:3]=[C:4]([C:10]2[O:11][CH:12]=[C:13]([CH2:15][CH2:16][C:17]([C:19]3[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=3)=[O:18])[N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9])[CH:28]=[CH2:27]

Participants

7

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68983174HCID 68983174, compound

Product 1

HCID 57855771HCID 57855771, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 0.3 g quantity of 3-[2-(3-hydroxy-4-methoxyphenyl)oxazol-4-yl]-1-(3-methylpyridin-2-yl)propan-1-one obtained in Example 136 and 0.3 ml of 1,8-diazabicyclo[5,4,0]undec-7-ene were dissolved in 6 ml of ethanol, 0.22 g of allyl bromide was added thereto, and the mixture was heated and refluxed for 4 hours. After standing to cool, water was added to the reaction mixture, and ethyl acetate extraction was performed. The extract was washed twice with water, the organic layer was then concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), thereby yielding 0.18 g of white powdery 3-[2-(3-allyloxy-4-methoxyphenyl)oxazol-4-yl]-1-(3-methylpyridin-2-yl)propan-1-one.

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 4 hours
  3. temperatureto cool
  4. washThe extract was washed twice with water
  5. concentrationthe organic layer was then concentrated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-8dfb24b58b13442c97a96c5135b8636b
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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