4'-Bromoacetanilide → Tert-butyl 2-({4-[(4-acetamidophenyl)ethynyl]phenyl}acetyl)hydrazinecarboxylate
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(NC(C)C)(C)C.Br[C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35](=[O:37])[CH3:36])=[CH:30][CH:29]=1.[C:38]([C:40]1[CH:45]=[CH:44][C:43]([CH2:46][C:47]([NH:49][NH:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])=[O:48])=[CH:42][CH:41]=1)#[CH:39]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[C:35]([NH:34][C:31]1[CH:32]=[CH:33][C:28]([C:39]#[C:38][C:40]2[CH:41]=[CH:42][C:43]([CH2:46][C:47]([NH:49][NH:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])=[O:48])=[CH:44][CH:45]=2)=[CH:29][CH:30]=1)(=[O:37])[CH3:36]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Palladium (II) acetate (2.5 mg, 0.011 mmol) and triphenylphosphine (11 mg, 0.044 mmol) were added to diisopropylamine (4 ml), and the mixture was stirred at room temperature for 20 mins. N-(4-Bromophenyl)acetamide (78 mg, 0.365 mmol) and tert-butyl 2-[(4-ethynylphenyl)acetyl]hydrazinecarboxylate (100 mg, 0.365 mmol) were added, and the mixture was stirred at 70° C. for 2 hrs. Anhydrous acetonitrile (2 ml) was added, and the mixture was further stirred at 70° C. for 1 hr. The reaction mixture was cooled and concentrated. The residue was purified by silica gel column chromatography (dichloromethane:methanol=97:3) to give tert-butyl 2-({4-[(4-acetamidophenyl)ethynyl]phenyl}acetyl)hydrazinecarboxylate (30 mg, yield 20%).
Workup
- stirringthe mixture was stirred at 70° C. for 2 hrs
- stirringthe mixture was further stirred at 70° C. for 1 hr
- temperatureThe reaction mixture was cooled
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=97:3)
Sources & evidence
- ORD record
- ord-561813911a7543208f638708e7d94705
- Source dataset
- uspto-grants-2015_04
- Patent number
- US08999989B2
Reaction notes
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