Phenyl-1-naphthylamine → N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine
Reaction equation
[C:1]1([NH:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:31][C:28]1[CH:29]=[CH:30][C:25]([C:22]2[CH:23]=[CH:24][C:19]([N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:8]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH:11]=[CH:10][CH:9]=3)=[CH:20][CH:21]=2)=[CH:26][CH:27]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A mixture of N-phenylnaphthalen-1-amine (4.41 g, 20 mmol), 4,4′-dibromo-1,1′-biphenyl (15 g, 48 mmol), sodium tert-butoxide (NaOBut) (4.8 g, 50 mmol) and Pd(dppf)Cl2 (0.44 g, 0.6 mmol) in anhydrous toluene (100 mL) was degassed and heated at 80° C. for about 10 hours. After cooling to RT, the mixture was poured into dichloromethane (400 mL) and stirred for about 30 min., then washed with brine (100 mL). The organic solution was collected and dried over Na2SO4, loaded on silica gel, and purified by flash column (hexanes to hexanes/ethyl acetate 90:1) to give a solid which was washed with methanol and dried under air to give a white solid Compound 4 (5.58 g, in 62% yield).
Workup
- customwas degassed
- temperatureAfter cooling to RT
- additionthe mixture was poured into dichloromethane (400 mL)
- washwashed with brine (100 mL)
- customThe organic solution was collected
- dry with materialdried over Na2SO4
- custompurified by flash column (hexanes to hexanes/ethyl acetate 90:1)
- customto give a solid which
- washwas washed with methanol
- customdried under air
Sources & evidence
- ORD record
- ord-bb1c2452679d4f3d8feb4e1f7f9f8309
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09172051B2
Reaction notes
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