Pyridine → 5-Bromo-4-chloro-2-isopropoxycarbonylamino-benzoic acid methyl ester

HRID 2353908Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2353908
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Br:10])[C:7]([Cl:11])=[CH:6][C:5]=1[NH2:12].N1C=CC=CC=1.[CH:20]([O:23][C:24](Cl)=[O:25])([CH3:22])[CH3:21]>ClCCl.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Br:10])[C:7]([Cl:11])=[CH:6][C:5]=1[NH:12][C:24]([O:23][CH:20]([CH3:22])[CH3:21])=[O:25]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 7917Isopropyl chloroformateHCID 53436879Methyl 2-amino-5-bromo-4-chlorobenzoate

Produkt 1

HCID 686794685-Bromo-4-chloro-2-isopropoxycarbonylamino-benzoic acid methyl esterAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-Amino-5-bromo-4-chloro-benzoic acid methyl ester (2.08 g, 7.86 mmol) and pyridine (1.91 ml, 23.6 mmol) in dichloromethane (75.0 ml) was added 1.00N isopropylchloroformate in toluene dropwise. The mixture was stirred for 16 hours at room temperature. The mixture washed with 0.500N HCl(aq) (100 ml), and brine (3×100 ml), then dried (Na2SO4) and concentrated to an oil. Purification by silica gel chromatography (gradient eluent, 0-10% ethyl acetate in hexane) provided 5-Bromo-4-chloro-2-isopropoxycarbonylamino-benzoic acid methyl ester (2.53 g, 92%) as a white crystalline material. MS (ES+): 350, 352 (M+H).

Aufarbeitung

  1. washThe mixture washed with 0.500N HCl(aq) (100 ml), and brine (3×100 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated to an oil
  4. customPurification by silica gel chromatography (gradient eluent, 0-10% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0421f98e6dda4bdd8ebde184fd0830ac
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07749992B2

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