Sodium Carbonate → 4'-[3-(2-Methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid methyl ester

HRID 1617506Notes

Reaction equation

HRID 1617506 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=2)=[O:11])=[CH:4][CH:3]=1.[CH3:26][O:27][C:28]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)=[O:29].C(=O)([O-])[O-].[Na+].[Na+].[NH4+].[Cl-]>O1CCOCC1.O>[CH3:26][O:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([C:2]2[CH:3]=[CH:4][C:5]([CH:8]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:25])[CH2:9][C:10]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=3)=[O:11])=[CH:6][CH:7]=2)=[CH:32][CH:31]=1)=[O:29]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 27343694-Methoxycarbonylphenylboronic acidHCID 666681803-(4-Bromo-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one

Product 1

HCID 666667824'-[3-(2-Methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid methyl esterYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 3-(4-bromo-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one (400 mg), (4-methoxycarbonylphenyl)boronic acid (275 mg), dichlor(1,1′-bis(diphenyl-phosphino)-ferrocene)palladium (II) dichloromethane adduct (41 mg) in dioxane (3 mL) and water (2.6 mL) was added a 2 M aqueous sodium carbonate solution (1.52 mL). The mixture was stirred at 80° C. for 1.5 h. A saturated solution of NH4Cl was added, the phases were separated and the inorganic one was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 1:1) to yield the title compound as a yellow foam (400 mg, 88%), MS (ESI+): m/z=450.2063 ([M+H]+).

Workup

  1. customthe phases were separated
  2. extractionthe inorganic one was extracted with EtOAc (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 1:1)

Sources & evidence

ORD record
ord-c647b08a0c844d94b2a0dfc9f8b1609b
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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