Dichloromethane → HCID 67345595, compound

HRID 1629742Notes

Reaction equation

HRID 1629742 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([NH:8][C@@H:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([CH3:19])[CH:13]=2)[CH2:10][CH3:11])=[CH:4][C:3]=1[CH:20]([O:23][CH3:24])[O:21][CH3:22].[CH2:25](Cl)Cl.[Zn](C)C>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]>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C@H:9]([NH:8][C:5]2[CH:6]=[N:7][C:2]([CH3:25])=[C:3]([CH:20]([O:23][CH3:24])[O:21][CH3:22])[CH:4]=2)[CH2:10][CH3:11])=[CH:13][C:14]=1[CH3:19]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 86656228HCID 86656228, compoundHCID 178477796HCID 178477796, compound

Product 1

HCID 67345595HCID 67345595, 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

A mixture of INT 48 (250 mg, 0.677 mmol) and Pd(dppf)Cl2.CH2Cl2 (16.6 mg, 0.020 mmol) was dissolved in degassed dioxane (7 mL) and ZnMe2 (2 M in toluene, 1.02 mL, 2.04 mmol) was added. The mixture was stirred in a sealed vessel at 100° C. overnight. After cooling down, the mixture was quenched with a few drops of MeOH and the mixture was diluted with EtOAc, washed with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography (cyclohexane/EtOAc) to give INT 49.

Workup

  1. temperatureAfter cooling down
  2. customthe mixture was quenched with a few drops of MeOH
  3. additionthe mixture was diluted with EtOAc
  4. washwashed with saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (cyclohexane/EtOAc)
  8. customto give INT 49

Sources & evidence

ORD record
ord-55f20f3aacf74fd5a88adf428827089f
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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