Sodium Carbonate → HCID 117759986, compound

HRID 709841Notes

Reaction equation

HRID 709841 reaction equation
Br[C:2]1[S:6][C:5]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:15]([CH:21]3[CH2:23][CH2:22]3)[CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:12]=[CH:13][CH:14]=2)=[N:4][C:3]=1[C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1.[F:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][C:36]=1B(O)O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH:21]1([CH:15]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:7][C:5]3[S:6][C:2]([C:36]4[CH:37]=[C:38]([O:41][CH3:42])[CH:39]=[CH:40][C:35]=4[F:34])=[C:3]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)[N:4]=3)[CH:10]=2)[CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:23][CH2:22]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 41572112-Fluoro-5-methoxyphenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 117760221HCID 117760221, compound

Product 1

HCID 117759986HCID 117759986, compoundYield 96.3%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To methyl 3-(3-((5-bromo-4-(4-(trifluoromethyl)phenyl)thiazol-2-yl)methoxy)phenyl)-3-cyclopropylpropanoate (115 mg) in toluene (10 mL) were added (2-fluoro-5-methoxyphenyl)boronic acid (108 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (26 mg), tris(dibenzylideneacetone)dipalladium(0) (20 mg) and 2.0 M aqueous sodium carbonate solution (0.32 mL), and the mixture was stirred at 100° C. for 1 hr. The mixture was allowed to cool to room temperature, and water was added. The reaction mixture was extracted with ethyl acetate, and the extract was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (120 mg) as orange crystals.

Workup

  1. temperatureto cool to room temperature
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washthe extract was washed with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous sodium 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-8d1be6937dfa41cca800d9ad62bbe878
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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