Dichloromethane → tert-Butyl methyl 5-(5-methylpyridin-2-yl)isophthalate

HRID 888375Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 888375
Br[C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[Br-].[CH3:20][C:21]1[CH:22]=[CH:23][C:24]([Zn+])=[N:25][CH:26]=1.[K+].[K+].[K+].C(N(CC([O-])=O)CC(O)=O)CN(CC([O-])=O)CC([O-])=O.ClCCl>O1CCCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:20][C:21]1[CH:22]=[CH:23][C:24]([C:2]2[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=[C:6]([CH:14]=2)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[N:25][CH:26]=1

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 62717Edetate TripotassiumHCID 66896065Tert-butyl methyl 5-bromoisophthalateHCID 178427808HCID 178427808, Verbindung

Produkt 1

HCID 68499855tert-Butyl methyl 5-(5-methylpyridin-2-yl)isophthalate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418851HCID 178418851, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of tert-butyl methyl 5-bromoisophthalate (10.6 g, 33.6 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.31 g, 0.61 mmol) in tetrahydrofuran (160 mL) was added 5-methyl-2-pyridylzinc bromide (0.5 M in THF; 121 mL, 60.5 mmol). The reaction mixture was heated to 60° C. After 18 h, the reaction was cooled to ambient temperature. Aqueous ethylenediaminetetraacetic acid tripotassium salt (0.4 M, 100 mL) and dichloromethane (100 mL) were added. The mixture was stirred for 15 min and the organic solvent was evaporated. The mixture was extracted with dichloromethane (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (99% hexanes/ethyl acetate→50% hexanes/ethyl acetate) gave the title compound. MS 328.1 (M+1).

Aufarbeitung

  1. temperaturethe reaction was cooled to ambient temperature
  2. customthe organic solvent was evaporated
  3. extractionThe mixture was extracted with dichloromethane (3×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (99% hexanes/ethyl acetate→50% hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-11bf9e874481447b84115655bc675d74
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247401B2

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