Phenyl-1-naphthylamine → HCID 22222674, compound

HRID 871819Notes

Reaction equation

HRID 871819 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[NH:10]([C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC([O-])(C)C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>CC([O-])=O.CC([O-])=O.[Pd+2].CC1C=CC=CC=1C>[C:17]1([N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 7013Phenyl-1-naphthylamineHCID 707414-BromobenzaldehydeHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxide

Product 1

HCID 22222674HCID 22222674, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

4-Bromobenzaldehyde (1.00 g, 5.40 mmol), 1-anilinonaphthalene (1.42 g, 6.48 mmol) and Pd(OAc)2 (25 mg, 0.11 mmol) and NaOtBu (623 mg, 6.48 mmol) were charged in a sealed tube. The sealed tube was deoxygenated and purged with nitrogen, and added dried o-xylene (30 mL) and tri-tert-butylphosphine (0.23 ml, 0.11 mmol). The reaction was heated to 120° C., and stirred for 48 hours. The resulting was filtered to remove metal and then concentrated under reduced pressure and the residue was purified by column chromatography (hexanes/CH2Cl2=1/1) to afford F (1.10 g, 63%) as yellow solid.

Workup

  1. customThe sealed tube was deoxygenated
  2. custompurged with nitrogen
  3. filtrationThe resulting was filtered
  4. customto remove metal
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by column chromatography (hexanes/CH2Cl2=1/1)
  7. customto afford F (1.10 g, 63%) as yellow solid

Sources & evidence

ORD record
ord-281b3d5fcf384895a9d1828515937d9f
Source dataset
uspto-grants-2015_03
Patent number
US08974920B2

Reaction notes

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