tert-Butanol → (4-Bromo-6-methoxy-quinolin-3-yl)-carbamic acid tert-butyl ester

HRID 2356321Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2356321
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1C(O)=O.C([N:19]([CH2:22]C)CC)C.[C:24]([OH:28])([CH3:27])([CH3:26])[CH3:25].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:36])C=CC=CC=1>CN(C=O)C>[C:24]([O:28][C:22](=[O:36])[NH:19][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[Br:1])=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)([CH3:27])([CH3:26])[CH3:25]

Komponenten

6

Edukt 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 684531854-Bromo-6-methoxyquinoline-3-carboxylic acid

Produkt 1

HCID 68455075(4-Bromo-6-methoxy-quinolin-3-yl)-carbamic acid tert-butyl esterAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 4-Bromo-6-methoxyquinoline-3-carboxylic acid (34 g, 0.121 mole), triethylamine (141 mL) and tert-butanol (181 mL) in dry DMF (400 mL) was added diphenylphosphoryl azide (36.6 g, 28.6 mL, 0.133 mole). The mixture was heated at 100° C. for 1 h (see Note), then cooled and concentrated. The residue was dissolved in CH2Cl2 and washed with water (some insoluble material was removed by filtration). The aqueous phase was extracted with dichloromethane and the combined organics were dried (Na2SO4) and concentrated. Chromatography on silica gel (1 kg, 1:1 ether/light petroleum ether) gave the carbamate (22.7 g, 53%): MS (ES) m/e 309/311 (M+H)+, 354/6.

Aufarbeitung

  1. temperaturecooled
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with water (some insoluble material
  5. customwas removed by filtration)
  6. extractionThe aqueous phase was extracted with dichloromethane
  7. dry with materialthe combined organics were dried (Na2SO4)
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-73f28d42e0784ac68708013633cd460c
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759340B2

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