Quinoline → 2-Bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-amine

HRID 573549Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 573549
[NH2:1][C:2]1[C:7](C(O)=O)=[C:6]([CH3:11])[N:5]=[C:4]2[S:12][C:13]([Br:23])=[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)[C:3]=12.N1C2C(=CC=CC=2)C=CC=1>[Cu]>[Br:23][C:13]1[S:12][C:4]2[N:5]=[C:6]([CH3:11])[CH:7]=[C:2]([NH2:1])[C:3]=2[C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1

Komponenten

4

Edukt 2

HCID 7047QuinolineHCID 683238684-Amino-2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylic acid

Produkt 1

HCID 683240582-Bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-amineAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23978CopperKatalysator

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A mixture of 4-amino-2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylic acid (400 mg, 1.017 mmol) (Description 16), copper (194 mg, 3.05 mmol) and quinoline (3 mL, 25.3 mmol) was heated in a microwave at 180° C. for 30 min and then 190° C. for 30 min. After cooling to RT, the mixture was purified by chromatography on silica gel, eluting with a gradient of 40-60% ethyl acetate in cyclohexane, to give the title compound (214 mg). LCMS (A) m/z: 349/351 [M+1]+, Rt 1.08 min (acidic).

Aufarbeitung

  1. temperatureAfter cooling to RT
  2. customthe mixture was purified by chromatography on silica gel
  3. washeluting with a gradient of 40-60% ethyl acetate in cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-83200aecb0384ab2b49f9394b28c7c20
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029545B2

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