Potassium Phosphate, Tribasic → HCID 57709060, compound

HRID 547051Notes

Reaction equation

HRID 547051 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:75]1[CH:80]=[CH:79][C:78](B2OC(C)(C)C(C)(C)O2)=[C:77]([CH3:90])[CH:76]=1)([C:55]1[CH:60]=[CH:59][C:58]([C:61]#[C:62][C:63]2([O:69][Si:70]([CH3:73])([CH3:72])[CH3:71])[CH2:68][CH2:67][S:66][CH2:65][CH2:64]2)=[C:57]([CH3:74])[CH:56]=1)[CH2:53][CH3:54])[CH3:51]>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:78]2[CH:79]=[CH:80][C:75]([C:52]([CH2:53][CH3:54])([C:55]3[CH:60]=[CH:59][C:58]([C:61]#[C:62][C:63]4([O:69][Si:70]([CH3:71])([CH3:73])[CH3:72])[CH2:68][CH2:67][S:66][CH2:65][CH2:64]4)=[C:57]([CH3:74])[CH:56]=3)[CH2:50][CH3:51])=[CH:76][C:77]=2[CH3:90])=[CH:7][CH:6]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 316783Methyl 2-(4-bromophenyl)acetateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57709123HCID 57709123, compound

Product 1

HCID 57709060HCID 57709060, compoundYield 89.7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

(4-Bromo-phenyl)acetic acid methyl ester (35 mg, 0.15 mmol), palladium acetate (2.3 mg, 0.01 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (8.3 mg, 0.02 mmol), potassium phosphate (65 mg, 0.3 mmol) and water (0.2 mL) were added to a solution of 2-(4-{1-ethyl-1-[3-methyl-4-(4-trimethylsilanyloxy-tetrahydro-thiopyran-4-ylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Example 136-(4); 60 mg, 0.1 mmol) in toluene (2 mL). The mixture was stirred in a nitrogen atmosphere at 110° C. for two hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. 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=1:1) to give the target compound as a colorless oil (55 mg, 88%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  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=1:1)

Sources & evidence

ORD record
ord-d87e1846ea7c4d73b67785152ce049f2
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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