Ethanol → HCID 23025001, compound

HRID 350118Notes

Reaction equation

HRID 350118 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:41]=[CH:40][C:18]([CH2:19][N:20]2[CH:24]=[C:23]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:22](OS(C(F)(F)F)(=O)=O)=[N:21]2)=[CH:17][CH:16]=1.[CH3:42][O:43][C:44]1[CH:49]=[CH:48][C:47](B(O)O)=[CH:46][CH:45]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:42][O:43][C:44]1[CH:49]=[CH:48][C:47]([C:22]2[C:23]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:24][N:20]([CH2:19][C:18]3[CH:40]=[CH:41][C:15]([O:14][CH2:13][C:3]4[N:4]=[C:5]([C:7]5[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=5)[O:6][C:2]=4[CH3:1])=[CH:16][CH:17]=3)[N:21]=2)=[CH:46][CH:45]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 86760425HCID 86760425, compound

Product 1

HCID 23025001HCID 23025001, compoundYield 24.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (790 mg) was added to a mixture of ethyl 3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-trifluoromethanesulfonyloxy-1H-pyrazol-4-yl]propionate (2.00 g), 4-methoxyphenylboronic acid (0.77 g), 2N aqueous sodium carbonate solution (5.0 ml), ethanol (5 ml), and toluene (100 ml). This mixture was refluxed under an argon atmosphere for 13 hours. Ethyl acetate was added to the reaction mixture, which was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-[3-(4-methoxyphenyl)-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propionate (450 mg, yield: 24%) was obtained as an oily substance from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. temperatureThis mixture was refluxed under an argon atmosphere for 13 hours
  2. washwas washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a3f773f459fc42b0972f0f75dae9a3f5
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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