Diphenylamine → HCID 59270601, compound

HRID 446218Notes

Reaction equation

HRID 446218 reaction equation
[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:9]2[CH:14]=[CH:13][C:12](Br)=[CH:11][CH:10]=2)=[O:8])[CH:2]=1.[C:22]1([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C>C1(C)C=CC=CC=1.[Pd].[Pd].CC(C)=O>[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([N:28]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:11][CH:10]=2)=[O:8])[CH:2]=1

Participants

6

Reactant 3

HCID 11487DiphenylamineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 4217227HCID 4217227, compound

Product 1

HCID 59270601HCID 59270601, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 131730690HCID 131730690, compoundCatalystHCID 1140TolueneSolvent

Procedure

Biphenyl-3-yl(4-bromophenyl)methanone (5.0 g, 14.83 mmol) and diphenylamine (3.8 g, 22.2 mmol) were dissolved in toluene (150 mL) under a nitrogen atmosphere, and then tris(benzylidine acetone dipalladium) (0.3 g, 0.3 mmol) was added thereto under nitrogen. Also, P(t-Bu)3 (0.3 g, 1.5 mmol) was added to the reaction mixture solution, followed by addition of NaOBut (4.3 g, 44.5 mmol). The reaction mixture solution was refluxed and stirred for 24 hours. After the reaction was over, the reaction mixture solution was filtered through a thin silica pad at a high temperature to thereby remove palladium. The filtrate was concentrated, and was passed through a silica gel column by using hexane-dichloromethane 7:3 as an eluant. After the solvent was removed, the residue material was dried in vacuum to thereby obtain a white solid (5.1 g, yield: 81%).

Workup

  1. additionfollowed by addition of NaOBut (4.3 g, 44.5 mmol)
  2. temperatureThe reaction mixture solution was refluxed
  3. filtrationwas filtered through a thin silica pad at a high temperature to thereby remove palladium
  4. concentrationThe filtrate was concentrated
  5. customAfter the solvent was removed
  6. customthe residue material was dried in vacuum

Sources & evidence

ORD record
ord-2ac61ccccd5642b995063ef0738eb2b3
Source dataset
uspto-grants-2013_07
Patent number
US08476474B2

Reaction notes

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