Phenolate Sodium → HCID 178461349, compound

HRID 1826903Notes

Reaction equation

HRID 1826903 reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12](Br)[N:11]=2)[CH2:4][CH2:3]1.[O-:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Na+]>C1(C)C=CC=CC=1.O1CCCC1.C(OCC)(=O)C>[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:11]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 4445035Phenolate SodiumHCID 178461348HCID 178461348, compound

Product 1

HCID 178461349HCID 178461349, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

A nitrogen purged mixture of N-(trans-4-methylcyclohexyl)-6-bromo picolinamide (446 mg, 1.5 mmol), sodium phenoxide (209 mg, 1.8 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalldium(II) (1:1 complex with dichloromethane; 83 mg, 0.1 mmol) in toluene-tetrahydrofuran (9:1, 5 mL) was treated with bis(dibenzylideneacetone)palladium(II) (86 mg, 0.15 mmol) and the mixture heated at reflux overnight. After this time the reaction mixture was diluted with ethyl acetate (25 mL) and filtered. The organic solution was washed with water (2×20 mL), brine, dried over anhydrous MgSO4, filtered and concentrated. Chromatography of the crude product on silica (2 mm, chromatotron) with ethyl acetate-hexane (1:3, containing 1% diethylamine) afforded 97 mg (21%) of 410:

Workup

  1. customA nitrogen purged
  2. temperaturethe mixture heated
  3. temperatureat reflux overnight
  4. filtrationfiltered
  5. washThe organic solution was washed with water (2×20 mL), brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ddb0872209cd4de5a8cead25b08fc0cf
Source dataset
uspto-grants-2006_05
Patent number
US07053104B2

Reaction notes

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