Potassium Phosphate, Tribasic → HCID 57709156, compound

HRID 547093Notes

Reaction equation

HRID 547093 reaction equation
[C:1]([Si:5]([O:8][CH:9]([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH2:41][CH3:42])([C:25]2[CH:30]=[CH:29][C:28](B3OC(C)(C)C(C)(C)O3)=[C:27]([CH3:40])[CH:26]=2)[CH2:23][CH3:24])=[CH:18][C:17]=1[CH3:43])[C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[CH3:44][O:45][C:46](=[O:56])[CH:47]([C:49]1[CH:54]=[CH:53][C:52](Br)=[CH:51][CH:50]=1)[OH:48].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:44][O:45][C:46](=[O:56])[CH:47]([C:49]1[CH:54]=[CH:53][C:52]([C:28]2[CH:29]=[CH:30][C:25]([C:22]([C:19]3[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][CH:9]([O:8][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:6])[CH3:7])[C:10]([CH3:13])([CH3:12])[CH3:11])=[C:17]([CH3:43])[CH:18]=3)([CH2:23][CH3:24])[CH2:41][CH3:42])=[CH:26][C:27]=2[CH3:40])=[CH:51][CH:50]=1)[OH:48]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 14571696Methyl 4-bromo-alpha-hydroxybenzeneacetateHCID 577089262-[4-(1-{4-[3-(t-Butyldimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Product 1

HCID 57709156HCID 57709156, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
91 °C

Procedure

Degassed N,N-dimethylformamide (0.26 mL) was added to t-butyl-(1-{2-[4-(1-ethyl-1-{4-[4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl]-3-methyl-phenyl}-propyl)-2-methyl-phenyl]-ethyl}-2,2-dimethyl-propoxy)dimethylsilane (Example 24-(1); 22.4 mg, 0.0343 mmol), 4-bromo-phenyl-hydroxy-acetic acid methyl ester (Example 154-(1); 10.5 mg, 0.0428 mmol), tetrakis(triphenylphosphine)palladium (0) (6.2 mg, 0.0054 mmol) and potassium phosphate (14.1 mg, 0.0664 mmol). After replacement with nitrogen, the mixture was heated while stirring at an external temperature of 86 to 96° C. for five hours. Water was added to the reaction mixture, followed by extraction with diethyl ether. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=7/1) to give the title compound (7.0 mg, 32%).

Workup

  1. customDegassed N,N-dimethylformamide (0.26 mL)
  2. temperatureAfter replacement with nitrogen, the mixture was heated
  3. extractionfollowed by extraction with diethyl ether
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=7/1)

Sources & evidence

ORD record
ord-6f9b791aae074224a5a68ee9e5025271
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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