Potassium Carbonate → HCID 68999756, compound

HRID 1821340Notes

Reaction equation

HRID 1821340 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2Br)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:26]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)(=[O:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C.O>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N:32]2[CH2:33][CH2:34][N:29]([C:26](=[O:28])[CH3:27])[CH2:30][CH2:31]2)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 837951-AcetylpiperazineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 68998360HCID 68998360, compound

Product 1

HCID 68999756HCID 68999756, compoundYield 17%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
121 °C

Procedure

To a solution of (E)-3-[2-(2-bromophenyl)vinyl]indazole-1-carboxylic acid tert-butyl ester (0.23 g, 0.57 mmol) obtained in Step 2 in toluene (1.5 mL), 1-acetylpiperazine (0.15 g, 1.1 mmol), potassium carbonate (0.20 mg, 1.4 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphane (0.068 g, 0.14 mmol) and tris(dibenzylideneacetone)dipalladium (0.052 g, 0.57 mmol) were sequentially added and, the mixture was stirred at 121° C. for 10 minutes under microwave (300 W) irradiation. The reaction mixture was added with water and ethyl acetate to separate the mixture into organic layer and aqueous layer and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 50/50) to obtain (E)-3-{2-[2-(4-acetylpiperazin-1-yl)phenyl]vinyl}indazol-1-carboxylic acid tert-butyl ester (0.042 g, 17%).

Workup

  1. customto separate the mixture into organic layer and aqueous layer
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 50/50)

Sources & evidence

ORD record
ord-3f7aa55ceb32467b96145ca13a3da0fc
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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