Sodium Carbonate → 4-(Pyridin-4-yl)naphth-1-ylamine

HRID 1936707

Reaction equation

HRID 1936707 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH2:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[N:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:19]1[CH:24]=[CH:23][C:22]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([NH2:12])=[CH:4][CH:3]=2)=[CH:21][CH:20]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 753034-Bromo-1-naphthylamineHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 108570124-(Pyridin-4-yl)naphth-1-ylamineYield 78.7%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred suspension of 4-bromonaphth-1-ylamine (10 g, 45 mmole) in 1,2-dimethoxyethane (400 ml) and water (100 ml) containing sodium carbonate (14 g) was flushed with argon for 0.3 hours. Tetrakis(triphenylphosphine) palladium (0) (2.75 g, 2.4 mmole) was added followed by pyridin-4-ylboronic acid (5.7 g, 46 mmole) and the mixture heated at reflux for 5 hours. The mixture was concentrated in vacuo to a brown slurry and partitioned between dichloromethane and water. The aqueous was further extracted with dichloromethane and the combined organics dried (Na2SO4) and concentrated in vacuo to a brown solid (13.2 g). Purification of the solid by flash chromatography eluting with ethyl acetate afforded the title compound as a yellow crystalline solid (7.8 g, 78%).

Workup

  1. customwas flushed with argon for 0.3 hours
  2. temperaturethe mixture heated
  3. temperatureat reflux for 5 hours
  4. concentrationThe mixture was concentrated in vacuo to a brown slurry
  5. custompartitioned between dichloromethane and water
  6. extractionThe aqueous was further extracted with dichloromethane
  7. dry with materialthe combined organics dried (Na2SO4)
  8. concentrationconcentrated in vacuo to a brown solid (13.2 g)
  9. customPurification of the solid by flash chromatography
  10. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-1870494c508f446d85291f9137834446
Source dataset
uspto-grants-2002_05
Patent number
US06391891B1

Linked notes

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