Tricyclohexylphosphine → HCID 58047666, compound

HRID 1888786Notes

Reaction equation

HRID 1888786 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[O:25][CH2:26][CH3:27])[CH2:5][O:6][C:7]1[CH:21]=[CH:20][C:10]2[CH:11]=[C:12]([CH:14]([NH:16][C:17](=[O:19])[CH3:18])[CH3:15])[O:13][C:9]=2[CH:8]=1.[CH:28]1(B(O)O)[CH2:30][CH2:29]1.C(O[K])(C)(C)C.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:28]1([C:2]2[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=2[O:25][CH2:26][CH3:27])[CH2:5][O:6][C:7]2[CH:21]=[CH:20][C:10]3[CH:11]=[C:12]([CH:14]([NH:16][C:17](=[O:19])[CH3:18])[CH3:15])[O:13][C:9]=3[CH:8]=2)[CH2:30][CH2:29]1

Participants

8

Reactant 5

HCID 75806TricyclohexylphosphineHCID 516892Sodium BicarbonateHCID 2760897Cyclopropylboronic acidHCID 58047446HCID 58047446, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 58047666HCID 58047666, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A solution of N-(1-{6-[(3-bromo-4-ethoxybenzyl)oxy]-1-benzofuran-2-yl}ethyl)acetamide (100 mg, 0.231 mmol) obtained in Example 175, cyclopropylboronic acid (58.9 mg, 0.693 mmol), tert-butoxy potassium (77.6 mg, 0.693 mmol), tricyclohexylphosphine (6.50 mg, 0.0231 mmol) and palladium(II) acetate (2.60 mg, 0.0115 mmol) in toluene (4 mL) was stirred under argon at 100° C. overnight. To the reaction mixture was added aqueous sodium hydrogen carbonate solution, and the mixture was extracted twice with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1) and triturated with a small amount of hexane and diisopropyl ether to give the title compound (54.6 mg, yield 60%) as a white solid.

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1)
  6. customtriturated with a small amount of hexane and diisopropyl ether

Sources & evidence

ORD record
ord-9ba05f9fbb0a42a395c160b6605cc18f
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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