Methanol → HCID 22678776, compound

HRID 1837741Notes

Reaction equation

HRID 1837741 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17]([C:19]3[S:20][CH:21]=[CH:22][C:23]=3Br)=[O:18])[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1.[C:25]1(OB(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CO.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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.O>[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17](=[O:18])[C:19]3[S:20][CH:21]=[CH:22][C:23]=3[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 22678700HCID 22678700, compound

Product 1

HCID 22678776HCID 22678776, compoundYield 100.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

290 mg of 1-[(2-methoxy-3-pyridyl)methyl]-4-[2-(3-bromo-2-thienyl)-2-oxoethyl]piperidine obtained in Example 73, 173 mg of phenylboric acid and 42 mg of tetrakis(triphenylphosphine)palladium were suspended in 5.6 ml of toluene, 1.4 ml of methanol and 2.8 ml of 2 M sodium carbonate, and the mixture was heated under reflux for 3 hours under nitrogen flow. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by silica gel column chromatography (ethyl acetate), to give 290 mg of the title compound as a yellow oil.

Workup

  1. temperatureunder reflux for 3 hours under nitrogen flow
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe crude product was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-f00160a63bee4fdabcc0623f234b52d7
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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