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Cesium carbonate → HCID 68525258, compound

HRID 1932427
Notes
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Reaction equation

HRID 1932427 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:13][O:14][CH3:15])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH2:16]([N:23]1[CH2:28][CH2:27][N:26]([C:2]2[CH:3]=[CH:4][C:5]([O:12][CH2:13][O:14][CH3:15])=[C:6]([CH:11]=2)[C:7]([O:9][CH3:10])=[O:8])[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 759941-BenzylpiperazineHCID 634876Binap, (A+-)-HCID 20827868HCID 20827868, compound

Product 1

HCID 68525258HCID 68525258, compound

Reagents, catalysts & solvents 3

HCID 167845
palladium(II) acetate
Catalyst
HCID 962WaterSolvent
HCID 1140TolueneSolvent

Procedure

To a solution of methyl 5-chloro-2-methoxymethoxybenzoate (1.45 g, 6.29 mmol) and 1-benzylpiperazine (1.66 g, 9.43 mmol) in toluene (50 mL) were added palladium acetate (28 mg, 0.126 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (157 mg, 0.252 mmol) and cesium carbonate (3.07 g, 9.43 mmol), and the resulting solution was refluxed for 3 hours. Water was added to the resulting solution, and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:2), to thereby yield 400 mg of the title compound.

Workup

  1. temperaturethe resulting solution was refluxed for 3 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:2)

Sources & evidence

ORD record
ord-f41ef6500ace4e438c81c76975516bea
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08188277B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes