Water → 5-(Benzyloxy)-2-(2-fluoro-5-methoxyphenyl)-3-neopentylpyridine

HRID 1049468Notes

Reaction equation

HRID 1049468 reaction equation
FC(F)(F)S(O[C:7]1[C:12]([CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:11][C:10]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:9][N:8]=1)(=O)=O.[F:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>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>[CH2:19]([O:18][C:10]1[CH:11]=[C:12]([CH2:13][C:14]([CH3:15])([CH3:16])[CH3:17])[C:7]([C:30]2[CH:31]=[C:32]([O:35][CH3:36])[CH:33]=[CH:34][C:29]=2[F:28])=[N:8][CH:9]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 41572112-Fluoro-5-methoxyphenylboronic acidHCID 1177600275-(Benzyloxy)-3-neopentylpyridin-2-yl trifluoromethanesulfonate

Product 1

HCID 1177596905-(Benzyloxy)-2-(2-fluoro-5-methoxyphenyl)-3-neopentylpyridineYield 93.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Under an argon atmosphere, to a solution of 5-(benzyloxy)-3-neopentylpyridin-2-yl trifluoromethanesulfonate (3.35 g) in toluene (25 mL) were added (2-fluoro-5-methoxyphenyl)boronic acid (2.12 g), tetrakis(triphenylphosphine)palladium (0) (961 mg) and 2.0 M aqueous sodium carbonate solution (12.5 mL), and the mixture was stirred at 90° C. for 3 hr. Water was added at room temperature, and the mixture was filtered through celite. The filtrate was extracted with ethyl acetate, and the extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.95 g) as a pale-yellow oil.

Workup

  1. filtrationthe mixture was filtered through celite
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washthe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4056dd28115247198cfdf9c81d45ec4f
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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