4-Bromoanisole → N-(4-Methoxyphenyl)-4-phenyl-1-naphthalenamine

HRID 503625Notes

Reaction equation

HRID 503625 reaction equation
CC(C)([O-])C.[Na+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.Br[C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1.[C:45]1([C:51]2[C:60]3[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=3)[C:54]([NH2:61])=[CH:53][CH:52]=2)[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C(Cl)Cl.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].O1CCOCC1>[CH3:44][O:43][C:40]1[CH:41]=[CH:42][C:37]([NH:61][C:54]2[C:55]3[C:60](=[CH:59][CH:58]=[CH:57][CH:56]=3)[C:51]([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)=[CH:52][CH:53]=2)=[CH:38][CH:39]=1

Participants

8

Reactant 4

HCID 77304-BromoanisoleHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 130872274-Phenylnaphthalen-1-amineHCID 23676156Sodium t-butoxide

Product 1

HCID 67318488N-(4-Methoxyphenyl)-4-phenyl-1-naphthalenamine

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A pyrex reaction tube was charged with sodium tert-butoxide (239 mg, 2490 μmol), Pd2(dba)3(81.4 mg, 88.9 μmol), S-Phos (146 mg, 356 μmol), 1-bromo-4-methoxybenzene (333 mg, 1779 μmol), 4-phenylnaphthalen-1-amine (390 mg, 1779 μmol) and dioxane. The tube was sealed and the mixture was stirred at 100° C. for 2 h. LCMS showed complete conversion to product. The mixture was diluted with DCM and washed with water. The organic portion was dried, filtered and concentrated. The crude material was passed through a plug of silica gel using 50% EtOAc/hex and the filtrate was concentrated to provide the desired product. MS: [M+H]=326.

Workup

  1. customThe tube was sealed
  2. washwashed with water
  3. customThe organic portion was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f0d079051ad246bc97ca2384cf8d663d
Source dataset
uspto-grants-2010_08
Patent number
US07776857B2

Reaction notes

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