Potassium Phosphate, Tribasic → HCID 57709130, compound

HRID 547022Notes

Reaction equation

HRID 547022 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:50]([C:52]([C:74]1[CH:79]=[CH:78][C:77](B2OC(C)(C)C(C)(C)O2)=[C:76]([CH3:89])[CH:75]=1)([C:55]1[CH:60]=[CH:59][C:58]([C:61]#[C:62][C:63]([CH2:71][CH3:72])([O:66][Si:67]([CH3:70])([CH3:69])[CH3:68])[CH2:64][CH3:65])=[C:57]([CH3:73])[CH:56]=1)[CH2:53][CH3:54])[CH3:51].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:77]2[CH:78]=[CH:79][C:74]([C:52]([CH2:53][CH3:54])([C:55]3[CH:60]=[CH:59][C:58]([C:61]#[C:62][C:63]([CH2:71][CH3:72])([O:66][Si:67]([CH3:68])([CH3:69])[CH3:70])[CH2:64][CH3:65])=[C:57]([CH3:73])[CH:56]=3)[CH2:50][CH3:51])=[CH:75][C:76]=2[CH3:89])=[CH:7][CH:6]=1

Participants

9

Reactant 5

HCID 62657Potassium Phosphate, TribasicHCID 316783Methyl 2-(4-bromophenyl)acetateHCID 516892Sodium BicarbonateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57709043HCID 57709043, compound

Product 1

HCID 57709130HCID 57709130, compoundYield 42.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

(4-Bromo-phenyl)acetic acid methyl ester (Tetrahedron Letters 44 (2003) 331-334; 27 mg, 0.118 mmol), palladium acetate (1.8 mg, 0.008 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (6.6 mg, 0.016 mmol), potassium phosphate (50 mg, 0.234 mmol) and water (0.2 mL) were added to a solution of 2-(4-{1-ethyl-1-[4-(3-ethyl-3-trimethylsilanyloxy-1-pentynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Example 125-(3); 44 mg, 0.078 mmol) in toluene (2 mL). After replacement with nitrogen, the mixture was stirred at 100° C. for one hour. The reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1) to give the target compound as a colorless oil (19.3 mg, 42%).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-0abba27a03904127bfda52d783187848
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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