Sodium Azide → 6-Azido-4-(4-bromo-2-chlorophenylamino)nicotinic acid tert-butyl ester

HRID 917022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 917022
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([O:9][C:10](=[O:27])[C:11]1[C:16]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=2[Cl:25])=[CH:15][C:14](Cl)=[N:13][CH:12]=1)([CH3:8])([CH3:7])[CH3:6]>CN(C=O)C.CCOC(C)=O>[C:5]([O:9][C:10](=[O:27])[C:11]1[C:16]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=2[Cl:25])=[CH:15][C:14]([N:1]=[N+:2]=[N-:3])=[N:13][CH:12]=1)([CH3:8])([CH3:6])[CH3:7]

Komponenten

5

Edukt 2

HCID 33557Sodium AzideHCID 865967784-(4-Bromo-2-chlorophenylamino)-6-chloronicotinic acid tert-butyl ester

Produkt 1

HCID 865967796-Azido-4-(4-bromo-2-chlorophenylamino)nicotinic acid tert-butyl esterAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Sodium azide (1.51 g, 23.2 mmol) was added to a mixture of 4-(4-bromo-2-chlorophenylamino)-6-chloronicotinic acid tert-butyl ester (40) (3.23 g, 7.73 mmol) in DMF (60 mL). The reaction mixture was heated to 80° C. and stirred for 16 hours. After cooling to room temperature, the reaction was diluted with EtOAc and washed with water, saturated NaHCO3 and brine. The organic layer was dried (Na2SO4) and concentrated. Purification by flash column chromatography using the Biotage system (CH2Cl2) (repeated) provided the desired product (41) (1.41 g, 43%).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. washwashed with water, saturated NaHCO3 and brine
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0c1af25135484eaaba703bff354359af
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07271178B2

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