Potassium Phosphate, Tribasic → 1,1-Dimethylethyl {[3'-({[(1,1-dimethylethyl)(dimethyl)silyl]-oxy}methyl)-4-methyl-3-biphenylyl]methyl}carbamate

HRID 564478Notes

Reaction equation

HRID 564478 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:17])=[C:6]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:7]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:26][C:27]([Si:30]([CH3:43])([CH3:42])[O:31][CH2:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1)([CH3:29])[CH3:28]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2CCCCC2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2OC)CCCCC1>[CH3:29][C:27]([Si:30]([CH3:43])([CH3:42])[O:31][CH2:32][C:33]1[CH:34]=[C:35]([C:2]2[CH:3]=[CH:4][C:5]([CH3:17])=[C:6]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:7]=2)[CH:36]=[CH:37][CH:38]=1)([CH3:26])[CH3:28]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 57813315tert-butyl N-[(5-bromo-2-methylphenyl)methyl]carbamateHCID 57813382[3-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acid

Product 1

HCID 578134201,1-Dimethylethyl {[3'-({[(1,1-dimethylethyl)(dimethyl)silyl]-oxy}methyl)-4-methyl-3-biphenylyl]methyl}carbamateYield 90.6%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 16079156(1R)-Dicyclohexyl(2'-methoxy-[1,1'-binaphthalen]-2-yl)phosphaneCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

1,1-Dimethylethyl [(5-bromo-2-methylphenyl)methyl]carbamate (2.7 g, 9.0 mmol), Pd(OAc)2 (81 mg, 0.36 mmol), dicyclohexyl[2′-(methyloxy)-1,1′-binaphthalen-2-yl]phosphane (216 mg, 0.45 mmol) and K3PO4 (2.5 g, 11.7 mmol) were dissolved in dioxane (50 mL). The mixture was heated at 80° C. for 30 min, and then [3-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acid (3.1 g, 11.7 mmol) was added. The mixture reaction was stirred at reflux for two days. The solvent was removed under reduced pressure, then diluted with CH2Cl2 (100 mL). The organic layer was washed with water (30 mL), brine (30 mL), and dried over Na2SO4. After removing the solvent, 3.6 g of the crude product 1,1-dimethylethyl {[3′-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-4-methyl-3-biphenylyl]methyl}carbamate was obtained. Yield: 90%.

Workup

  1. customThe mixture reaction
  2. temperatureat reflux for two days
  3. customThe solvent was removed under reduced pressure
  4. additiondiluted with CH2Cl2 (100 mL)
  5. washThe organic layer was washed with water (30 mL), brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. customAfter removing the solvent

Sources & evidence

ORD record
ord-407aa876ce22447c96c5cd90ff71fa5c
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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