1,4-Dichloro-5,6,7,8-tetrahydro-5,8-ethanophthalazine → HCID 87292593, compound

HRID 469522Notes

Reaction equation

HRID 469522 reaction equation
Cl[C:2]1[C:11]2[CH:10]3[CH2:12][CH2:13][CH:7]([CH2:8][CH2:9]3)[C:6]=2[C:5]([Cl:14])=[N:4][N:3]=1.[Zn](C(C)C)[CH:16]([CH3:18])[CH3:17]>O1CCOCC1>[CH:16]([C:2]1[C:11]2[CH:10]3[CH2:12][CH2:13][CH:7]([CH2:8][CH2:9]3)[C:6]=2[C:5]([Cl:14])=[N:4][N:3]=1)([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 64161071,4-Dichloro-5,6,7,8-tetrahydro-5,8-ethanophthalazineHCID 178461828HCID 178461828, compound

Product 1

HCID 87292593HCID 87292593, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1,4-dichloro-5,6,7,8-tetrahydro-5,8-ethanophthalazine (Alfa Aesar) (0.109 g, 0.474 mmol), iPr2Zn (1 M in toluene, 0.50 mL, 0.50 mmol), PdCl2dppf CH2Cl2 (19.3 mg, 0.024 mmol) in dioxane (1.5 mL) was stirred at 80° C. for 2.5 hours, quenched with 1 N HCl, diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine, dried (Na2SO4), and filtered. The residue was chromatographed on SiO2 (10% Et2O/CH2Cl2 to 5% MeOH/CH2Cl2) to give impure title compound as a tacky solid (34.9 mg). LC/MS (APCI) M/Z 237.1 (M+H)+.

Workup

  1. customquenched with 1 N HCl
  2. additiondiluted with EtOAc
  3. washwashed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe residue was chromatographed on SiO2 (10% Et2O/CH2Cl2 to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-6e02ca35a2c040e69f878abdeb1a1e16
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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