Potassium Hydroxide → HCID 66653210, compound

HRID 2400366Notes

Reaction equation

HRID 2400366 reaction equation
[C:1]([O:5][C:6](=[O:26])[CH2:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][C:13]2[O:16][C:17]([C:19]3[CH:24]=[CH:23][C:22](Br)=[CH:21][CH:20]=3)=[CH:18][C:12]=2[CH2:11]1)([CH3:4])([CH3:3])[CH3:2].[OH-:27].[K+].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C>C1(C)C=CC=CC=1.CCOC(C)=O.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]>[C:1]([O:5][C:6](=[O:26])[CH2:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][C:13]2[O:16][C:17]([C:19]3[CH:24]=[CH:23][C:22]([OH:27])=[CH:21][CH:20]=3)=[CH:18][C:12]=2[CH2:11]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 66653261HCID 66653261, compound

Product 1

HCID 66653210HCID 66653210, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Compound 7d (Rb=H, 4.91 g, 11.68 mmol) was dissolved in toluene (100 ml) and to the solution was added potassium hydroxide (2 ml, 11.7N) and the solution was degassed. To the solution was added 2-di-t-butylphosphino-2′,4′,6′-triisopropylbiphenyl (0.27 g, 0.64 mmol, 0.06 eq) and tris-(dibenzylideneaceton)-dipalladium(0) (0.29 g, 0.32 mmol, 0.03 eq). The mixture was stirred at 60° C. for 1.25 hrs. The mixture was cooled to room temperature, diluted with EtOAc and washed with 5% NaHCO3 solution (100 ml). The organic layers were dried on MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (diethyl ether/petroleum ether, 1/1 to 1/0, v/v, Rf 0.1) to give pure compound 8d (Rb=H, 4.0 g) as a yellow solid. LC-MS (Method A): Rt 1.21, [M+H] 358.

Workup

  1. customthe solution was degassed
  2. temperatureThe mixture was cooled to room temperature
  3. washwashed with 5% NaHCO3 solution (100 ml)
  4. customThe organic layers were dried on MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (diethyl ether/petroleum ether, 1/1 to 1/0, v/v, Rf 0.1)

Sources & evidence

ORD record
ord-573a2aa6adaa41a0acc10ad9c09041ff
Source dataset
uspto-grants-2014_08
Patent number
US08796262B2

Reaction notes

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