Tetrahydrofuran → Ethyl 3-(1-isopropylphthalazin-6-yl)-4-methylbenzoate

HRID 2357542Notes

Reaction equation

HRID 2357542 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:20]=[CH:21][C:22]=3[CH3:23])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.O1C[CH2:27][CH2:26][CH2:25]1.CN1CCCC1=O.C([Mg]Cl)(C)C>C(OCC)(=O)C.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3]>[CH:26]([C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:20]=[CH:21][C:22]=3[CH3:23])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1)([CH3:27])[CH3:25]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 13387N-methyl-2-pyrrolidoneHCID 59726010Ethyl 3-(1-chlorophthalazin-6-yl)-4-methylbenzoateHCID 178418918HCID 178418918, compound

Product 1

HCID 68455777Ethyl 3-(1-isopropylphthalazin-6-yl)-4-methylbenzoate

Reagents, catalysts & solvents 2

HCID 5483663Ferric acetylacetonateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 50-mL round-bottom flask under argon was charged with ethyl 3-(1-chlorophthalazin-6-yl)-4-methylbenzoate (106 mg, 0.32 mmol), iron(III) acetylacetonate (5.7 mg, 0.032 mmol), tetrahydrofuran (2.2 mL), and 1-methyl-2-pyrrolidinone (0.22 mL). Isopropylmagnesium chloride (0.24 mL, 0.49 mmol) was added via a syringe to the resulting red solution, causing an immediate color change to brown, and then finally to dark brown. The resulting mixture was stirred for 10 min, and the reaction was diluted with ethyl acetate and carefully quenched with 10% HCl solution. The mixture was washed with saturated aqueous NaHCO3 solution and the organic layer was dried (MgSO4) and concentrated in vacuo. CombiFlash purification (20% to 50% ethyl acetate in hexanes) afforded the title compound as a cream amorphous solid. MS (ES+): 335.2 (M+H)+.

Workup

  1. customcarefully quenched with 10% HCl solution
  2. washThe mixture was washed with saturated aqueous NaHCO3 solution
  3. dry with materialthe organic layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customCombiFlash purification (20% to 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6051fb5571734fc2bab3c77e31e742de
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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