Potassium Phosphate, Tribasic → HCID 57708938, compound

HRID 547077Notes

Reaction equation

HRID 547077 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9](Br)[CH:10]=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:70]1[CH:83]=[CH:82][C:73]([O:74][CH2:75][CH:76]([OH:81])[C:77]([CH3:80])([CH3:79])[CH3:78])=[C:72]([CH3:84])[CH:71]=1)([C:55]1[CH:60]=[CH:59][C:58](B2OC(C)(C)C(C)(C)O2)=[CH:57][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:6]=[N:7][CH:8]=[C:9]([C:58]2[CH:57]=[CH:56][C:55]([C:52]([CH2:50][CH3:51])([C:70]3[CH:83]=[CH:82][C:73]([O:74][CH2:75][CH:76]([OH:81])[C:77]([CH3:78])([CH3:79])[CH3:80])=[C:72]([CH3:84])[CH:71]=3)[CH2:53][CH3:54])=[CH:60][CH:59]=2)[CH:10]=1

Participants

9

Reactant 5

HCID 62657Potassium Phosphate, TribasicHCID 516892Sodium BicarbonateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23398394Methyl 2-(5-bromopyridin-3-yl)acetateHCID 574435301-(4-{1-Ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-ol

Product 1

HCID 57708938HCID 57708938, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

(5-Bromo-pyridin-3-yl)acetic acid methyl ester (Example 24-(2); 33.5 mg, 0.145 mmol), palladium acetate (2.2 mg, 0.010 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (8.2 mg, 0.020 mmol), potassium phosphate (62 mg, 0.291 mmol) and water (0.2 mL) were added to a solution of 1-(4-{1-ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-ol (Example 146-(1); 46.6 mg, 0.097 mmol) in toluene (2 mL). After replacement with nitrogen, the mixture was stirred at 100° C. for two hours. 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 (30.8 mg, 63%).

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-303c5e289fec4fb6b8f2a402558b52f0
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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