Toluene → HCID 22998665, compound

HRID 1166552Notes

Reaction equation

HRID 1166552 reaction equation
[ClH:1].Cl.Br[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH2:18][CH:17]([CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[CH2:16][CH2:15]3)=[CH:6][N:5]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:40][O:41][C:42]1[CH:47]=[CH:46][C:45](OB(O)O)=[CH:44][CH:43]=1>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[ClH:1].[ClH:1].[CH3:25][N:24]([CH2:23][CH2:22][CH:17]1[CH2:16][CH2:15][C:14]2[C:19](=[CH:20][CH:21]=[C:12]([O:11][CH2:10][C:7]3[CH:6]=[N:5][C:4]([C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=4[O:41][CH3:40])=[CH:9][CH:8]=3)[CH:13]=2)[CH2:18]1)[CH3:26]

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 147699944-Methoxyphenyl boric acidHCID 22998667HCID 22998667, compound

Product 1

HCID 22998665HCID 22998665, compoundYield 166.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of (+)-6-(2-bromopyridin-5-yl)methoxy-2-[2-(N,N-dimethylamino)ethyl]tetralin dihydrochloride (0.2 g), toluene (8 ml), ethanol (1 ml), 2M aqueous sodium carbonate (1 ml) was stirred at room temperature for 10 min. 4-methoxyphenylboric acid (89 mg), and tetrakis(triphenylphosphine)palladium (27 mg) was added and the reaction mixture was heated under reflux under argon for 15 hr and cooled. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried, and concentrated. The residue was purified by alumina column chromatography (eluent: ethyl acetate: hexane=1:4) and then converted into its dihydrochloride, which was recrystallized from ethanol-ethyl acetate to obtain the titled compound (176 mg).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux under argon for 15 hr
  3. temperaturecooled
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated aqueous sodium chloride
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by alumina column chromatography (eluent: ethyl acetate: hexane=1:4)
  9. customwas recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-9ef0f7fff27e4db2b71d2abfb750f949
Source dataset
uspto-grants-2003_09
Patent number
US06613805B2

Reaction notes

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