Potassium Carbonate → HCID 178439150, compound

HRID 564472Notes

Reaction equation

HRID 564472 reaction equation
[CH:1]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=C[CH:2]=1.C([O-])([O-])=O.[K+].[K+].Br[C:27]1[CH:28]=[C:29]([CH2:35][NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH:30]=[CH:31][C:32]=1[C:33]#N.[OH:44][CH2:45][C:46]1[CH:47]=[C:48](B(O)O)[CH:49]=[CH:50][CH:51]=1.[CH3:55][C:56]([Si:59](C)(C)[CH3:60])([CH3:58])[CH3:57]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:55][C:56]([SiH:59]([CH3:60])[O:44][CH2:45][C:46]1[CH:47]=[C:48]([C:27]2[C:32]([CH3:33])=[CH:31][CH:30]=[C:29]([CH2:35][NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH:28]=2)[CH:49]=[CH:50][CH:51]=1)([CH3:58])[CH3:57].[CH3:1][CH3:2]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 57813462HCID 57813462, compoundHCID 67006324HCID 67006324, compound

Product 1

HCID 178439150HCID 178439150, compoundYield 568%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

Pd(OAc)2 (56.3 mg, 0.25 mmol), PPh3 (263.0 mg, 1.0 mmol), K2CO3 (1.7 g, 12.5 mmol) and 1,1-dimethylethyl [(3-bromo-4-cyanophenyl)methyl]carbamate (2.6 g, 8.4 mmol) were suspended in 1,4-dioxane (30 mL). After the mixture was heated to 80° C. for 15 min, [3-(hydroxymethyl)phenyl]boronic acid-(1,1-dimethylethyl)(trimethyl)silane (2.7 g, 10.0 mmol) was added. Then the reaction mixture was stirred over night at 100° C. After cooled to room temperature, the solvent was removed under reduced pressure. The residue was dissolved in CH2Cl2 (50 mL), then washed with water (20 mL), brine (20 mL), and dried over Na2SO4. After the solvent was removed, the crude product was purified on Al2O3 column chromatography, eluting with CH2Cl2. 2.6 g of the product, 1,1-dimethylethyl{[3′-({[(1,1-dimethylethyl)(methyl)silyl]oxy}methyl)-6-methyl-3-biphenylyl]methyl}carbamate-ethane, was obtained (yield: 60%). 1H NMR (400 MHz, CDCl3): δ 0.12 (s, 6 H), 0.95 (s 9 H), 1.46 (s, 9 H), 4.41-4.42 (m, 2 H), 4.81 (s, 2 H), 7.37-7.47 (m, 6 H), 7.71 (d, J=8.0 Hz, 1 H); 13C NMR (100 MHz, CDCl3): δ −5.3, 18.4, 25.9, 28.3, 44.2, 64.7, 80.0, 109.9, 118.6, 126.1, 126.2, 126.4, 127.3, 128.6, 134.0, 137.9, 142.0, 144.5, 145.8, 155.8; HPLC: retention time: 9.500 min; purity: 95.2% (HPLC).

Workup

  1. temperatureAfter cooled to room temperature
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in CH2Cl2 (50 mL)
  4. washwashed with water (20 mL), brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. customAfter the solvent was removed
  7. customthe crude product was purified on Al2O3 column chromatography
  8. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-7355885c293e4ead93893f922334027b
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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