HCID 59302552, compound → HCID 66934111, compound

HRID 1019599Notes

Reaction equation

HRID 1019599 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH2:11][C:10]2[C:13](Br)=[CH:14][S:15][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].[Zn](C)[CH3:18]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH2:11][C:10]2[C:13]([CH3:18])=[CH:14][S:15][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 59302552HCID 59302552, compoundHCID 178477796HCID 178477796, compound

Product 1

HCID 66934111HCID 66934111, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

The product of step (f) (375 mg, 1.23 mmol) was dissolved in 4 mL dioxane and treated with Me2Zn (1.25 mL of 2M in toluene) and Pd(dppf)2Cl2. After heating to 100° C. for 3 h, the reaction was cooled, quenched with water, filtered through silica gel (washing with EtOAc), and concentrated to give 337 mg of the sub-title compound as an oil.

Workup

  1. temperaturethe reaction was cooled
  2. customquenched with water
  3. filtrationfiltered through silica gel (washing with EtOAc)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a27303f4584944f6b9e9009f43cf155a
Source dataset
uspto-grants-2014_05
Patent number
US08716276B2

Reaction notes

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