Diisopropylethylamine → HCID 67342449, Verbindung

HRID 451511

Reaktionsgleichung

Reaktionsgleichung von HRID 451511
IC1C=[CH:6][N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])C=1.[C:12]([N:19]1CCC(N)C[CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[CH3:26][CH2:27][N:28]([CH:32]([CH3:34])[CH3:33])[CH:29]([CH3:31])C>CN1C(=O)CCC1>[F:11][C:8]([F:9])([F:10])[C:4]1[CH:33]=[C:32]([N:28]2[CH2:27][CH2:26][CH:20]([NH:19][C:12](=[O:13])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:31][CH2:29]2)[CH:34]=[CH:6][N:5]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 234369404-Iodo-2-(trifluoromethyl)pyridine

Produkt 1

HCID 67342449HCID 67342449, VerbindungAusbeute 76,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

To a mixture of 4-iodo-2-(trifluoromethyl)pyridine (356 mg, 1.3 mmol) and Boc-4-aminopiperidine (340 mg, 1.7 mmol) in NMP (2.6 mL) was added DIPEA (319 L, 1.83 mmol). Argon was bubbled through the cloudy solution for 5 minutes before the reaction mixture was heated in the microwave for 3×30 minutes to 150° C. The mixture was then poured into water and extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and evaporated. Purification by chromatography (silica gel, 50 g, 0 to 100% ethyl acetate in heptane) afforded the title compound (343 mg, 76%) as a white solid.

Aufarbeitung

  1. customArgon was bubbled through the cloudy solution for 5 minutes before the reaction mixture
  2. temperaturewas heated in the microwave for 3×30 minutes to 150° C
  3. additionThe mixture was then poured into water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by chromatography (silica gel, 50 g, 0 to 100% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-97a5cba06aba46a4b17d85304e4b67f4
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486967B2

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