Potassium Phosphate, Tribasic → HCID 59494673, compound

HRID 872022Notes

Reaction equation

HRID 872022 reaction equation
Br[C:2]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:16][C:3]=1[CH2:4][N:5]([CH:13]1[CH2:15][CH2:14]1)[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[CH3:28]B1OB(C)OB(C)O1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH:13]1([N:5]([CH2:4][C:3]2[CH:16]=[C:17]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])[C:18]([O:20][CH3:21])=[CH:19][C:2]=2[CH3:28])[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH2:15][CH2:14]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 574072TrimethylboroxineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 59494587HCID 59494587, compound

Product 1

HCID 59494673HCID 59494673, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl [2-bromo-4-methoxy-5-(3-methoxypropoxy)benzyl]cyclopropylcarbamate (200 mg), trimethylboroxin (94 μL), tris(dibenzylideneacetone)dipalladium (8.2 mg), 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl (X-phos) (21.5 mg) and potassium phosphate (191 mg) in dioxane (7.0 ml) was stirred under argon atmosphere at 100° C. for 23 hours. After being stand to cool, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulted residue was purified with a NH-silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=10/1 to 3/1) to give tert-butyl cyclopropyl[4-methoxy-5-(3-methoxypropoxy)-2-methylbenzyl]carbamate (103 mg) as a pale yellow oil.

Workup

  1. temperatureto cool
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulted residue was purified with a NH-silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=10/1 to 3/1)

Sources & evidence

ORD record
ord-d75a15f42bc045caad1b03e617607f93
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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