Ethyl Acetate → 2-[2-(4-Bromo-2-chloro-phenoxy)-acetylamino]-isonicotinic acid methyl ester

HRID 1945433

Reaktionsgleichung

Reaktionsgleichung von HRID 1945433
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=O)=[C:4]([Cl:13])[CH:3]=1.[CH3:14][O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([NH2:23])[CH:18]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(OCC)(=O)C>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:14][O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:8](=[O:10])[CH2:7][O:6][C:5]2[CH:11]=[CH:12][C:2]([Br:1])=[CH:3][C:4]=2[Cl:13])[CH:18]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 236984Methyl 2-aminopyridine-4-carboxylateHCID 6931572-(4-Bromo-2-chlorophenoxy)acetic acidHCID 2724699PyBOP

Produkt 1

HCID 248120962-[2-(4-Bromo-2-chloro-phenoxy)-acetylamino]-isonicotinic acid methyl esterAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To solution of (4-bromo-2-chloro-phenoxyacetic acid (100 mg, 0.378 mmol), 2-amino isonicotinic acid methyl ester (86.42 mg, 0.568 mmol) and DMAP (69.43 mg, 0.568 mmol) in DMF 2 mL was added PyBOP (295 mg, 0.568 mmol) at room temperature. Reaction mixture was stirred at room temperature. Resulting mixture poured onto ice cold water, was diluted by ethyl acetate. The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by flash silica gel column chromatography (EtoAC:Hexane=1:9˜4:6) to give 2-[2-(4-bromo-2-chloro-phenoxy)-acetylamino]-isonicotinic acid methyl ester as a colorless solid (0.084 g, 56% yield).

Aufarbeitung

  1. customReaction mixture
  2. customResulting mixture
  3. additionpoured onto ice cold water
  4. customThe organic phase was separated
  5. washsequentially washed with aqueous sodium bicarbonate, brine and water
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by flash silica gel column chromatography (EtoAC:Hexane=1:9˜4:6)

Quellen und Nachweise

ORD-Eintrag
ord-f6c65c6971ce41d794aeffbb4f7fb94f
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394799B2

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