Water → HCID 118021299, Verbindung

HRID 1056616Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1056616
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](Cl)=[O:5].[Br:12][C:13]1[N:18]=[CH:17][C:16]([NH2:19])=[C:15]([CH3:20])[CH:14]=1.N1C=CC=CC=1.O>C(Cl)Cl>[Br:12][C:13]1[N:18]=[CH:17][C:16]([NH:19][C:4](=[O:5])[C:3]2[C:2]([F:1])=[CH:10][CH:9]=[CH:8][C:7]=2[F:11])=[C:15]([CH3:20])[CH:14]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 874382,6-Difluorobenzoyl chlorideHCID 199260946-Bromo-4-methylpyridin-3-amine

Produkt 1

HCID 118021299HCID 118021299, VerbindungAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a (0° C.) cooled and stirred solution of 2,6-difluorobenzoyl chloride (357 μL, 2.83 mmol) in DCM (5 mL) was added 6-bromo-4-methylpyridin-3-amine (583 mg, 3.12 mmol) followed by the addition of pyridine (344 μL, 4.25 mmol). The resulting mixture was then stirred at room temperature overnight. Water (5 mL) was added to the above mixture and then extracted with DCM (3×10 mL). The combined organic layers were washed with 10% aq.HCl (10 mL), dried (Na2SO4) and filtered. The filtrate was concentrated under vacuum to afford 650 mg (70%) of the title compound as a white solid. 1HNMR (400 MHz, DMSO-d6) δ 10.56 (s, 1H, D2O exchangeable), 8.41 (s, 1H), 7.66 (s, 1H), 7.65-7.58 (m, 1H), 7.27 (t, J=7.0 Hz, 2H), 2.27 (m, 3H); (ESI-MS (m/z) 327, 329 [(MH)+, Br79, 81].

Aufarbeitung

  1. extractionextracted with DCM (3×10 mL)
  2. washThe combined organic layers were washed with 10% aq
  3. dry with materialHCl (10 mL), dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-45472d6bd3874fa18fe40c9ead3b253a
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09399638B2

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