Sodium Carbonate → HCID 58401080, compound

HRID 1910347Notes

Reaction equation

HRID 1910347 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11](C)=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[F:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(COC)OC>[F:15][C:16]1[CH:21]=[C:20]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[CH:3]=2)[CH:19]=[CH:18][CH:17]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27339863-Fluorophenylboronic acidHCID 57668727HCID 57668727, compound

Product 1

HCID 58401080HCID 58401080, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 500 mL. three-necked round bottom flask equipped with a stir bar, temperature probe, and a nitrogen inlet were added 2-(3-bromophenyl)-5-methylpyridine (14.7 g, 60 mmol), 3-fluorophenylboronic acid (10.0 g, 72 mmol), palladium (II) acetate (0.335 g, 1.5 mmol), triphenylphosphine (1.56 g, 6.0 mmol), sodium carbonate (17.0 g, 160 mmol), containing dimethoxyethane (120 mL.) and water (80 mL.). The solution was heated at reflux for twenty hours, cooled, and diluted with ethyl acetate. The organic layer was separated, dried over magnesium sulfate, and evaporated to dryness to give a brown liquid, which was purified by flash silica gel chromatography using a 5/95 to 10/90 ethyl acetate/hexane gradient, yielding a viscous, colorless liquid (12.5 g 80%).

Workup

  1. customthree-necked round bottom flask equipped with a stir bar
  2. temperatureThe solution was heated
  3. temperatureat reflux for twenty hours
  4. temperaturecooled
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness
  8. customto give a brown liquid, which
  9. customwas purified by flash silica gel chromatography
  10. customyielding a viscous, colorless liquid (12.5 g 80%)

Sources & evidence

ORD record
ord-15ec8ffbb8e14f87a3ecf72f1302c25a
Source dataset
uspto-grants-2013_12
Patent number
US08603645B2

Reaction notes

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