Potassium Carbonate → HCID 57813523, compound

HRID 564479Notes

Reaction equation

HRID 564479 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+].Br[C:27]1[C:28]([CH3:42])=[C:29]([CH2:33][NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH:30]=[CH:31][CH:32]=1.[CH3:43][C:44]([Si:47]([CH3:60])([CH3:59])[O:48][CH2:49][C:50]1[CH:51]=[C:52](B(O)O)[CH:53]=[CH:54][CH:55]=1)([CH3:46])[CH3:45]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:46][C:44]([Si:47]([CH3:60])([CH3:59])[O:48][CH2:49][C:50]1[CH:51]=[C:52]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[C:28]=2[CH3:42])[CH:53]=[CH:54][CH:55]=1)([CH3:43])[CH3:45]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 57813382[3-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acidHCID 578133891177558-64-3

Product 1

HCID 57813523HCID 57813523, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Pd(OAc)2 (25.8 mg, 0.115 mmol), PPh3 (120.6 mg, 0.46 mmol), K2CO3 (794.0 mg, 5.75 mmol) and 1,1-dimethylethyl [(3-bromo-2-methylphenyl)methyl]carbamate (1.15 g, 3.85 mmol) were suspended in anhydrous 1,4-dioxane (20 mL) under nitrogen. After the mixture was heated to 60° C. for 30 min, [3-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acid (2.04 g, 4.62 mmol) was added. Then the mixture was stirred overnight at 100° C. After cooled to room temperature, the solvent was removed under reduced pressure. The residue was dissolved in EtOAc (20 mL), and then the solution was washed with water (7 mL), brine (7 mL), and, dried over anhydrous Na2SO4. After silica column chromatography, eluted with PE:EA=30:1, 1.1 g of the product was obtained, as a colorless liquid. (Yield: 65%). 1H NMR (400 MHz, CDCl3): 0.10 (s, 6 H), 0.94 (s, 9 H), 1.47 (s, 9 H), 2.19 (s, 3 H), 4.38 (d, J=5.2 Hz, 2 H), 4.76 (br, 1 H), 4.78 (s, 2 H), 7.14-7.39 (m, 7 H). 13C NMR (100 MHz, CDCl3): δ −5.2, 16.1, 18.4, 25.9, 28.4, 43.4, 64.9, 79.4, 124.6, 125.6, 127.0, 127.9, 129.3, 133.7, 136.9, 141.2, 141.9, 143.0, 155.7; HPLC: retention time: 4.987 min; purity: 98.9% (HPLC).

Workup

  1. temperatureAfter cooled to room temperature
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc (20 mL)
  4. washthe solution was washed with water (7 mL), brine (7 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. washAfter silica column chromatography, eluted with PE

Sources & evidence

ORD record
ord-8997e7e46d9a4012b917d6ba6cc75b37
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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