Triethylamine → HCID 86723309, Verbindung

HRID 2366218

Reaktionsgleichung

Reaktionsgleichung von HRID 2366218
[Cl:1][C:2]1[C:7]([F:8])=[C:6]([NH2:9])[CH:5]=[CH:4][N:3]=1.[Cl:10][C:11]1[CH:19]=[C:18]([I:20])[CH:17]=[C:16]([Cl:21])[C:12]=1[C:13](Cl)=[O:14].C(N(CC)CC)C>O1CCOCC1>[Cl:10][C:11]1[CH:19]=[C:18]([I:20])[CH:17]=[C:16]([Cl:21])[C:12]=1[C:13]([NH:9][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:7]=1[F:8])=[O:14]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 601502892-Chloro-3-fluoropyridin-4-amineHCID 866489582,6-Dichloro-4-iodobenzoyl chloride

Produkt 1

HCID 86723309HCID 86723309, VerbindungAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2-chloro-3-fluoropyridin-4-ylamine (1.73 g, 11.8 mmol), 2,6-dichloro-4-iodobenzoyl chloride (5.90 g, 17.65 mmol) and triethylamine (3.1 mL, 22.4 mmol) in dioxane (35 mL) was heated to 100° C. for 18 hours. The reaction mixture was partitioned between EtOAc and water. The organic layer washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The resultant residue was triturated with diethyl ether and dried under reduced pressure to give the desired compound as a pink solid (2.83 g, 54% yield). 1H NMR (300 MHz, CDCl3): δ 8.49-8.43 (m, 1H), 8.22 (d, J=5.5 Hz, 1H), 7.82-7.73 (m, 2H).

Aufarbeitung

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. washThe organic layer washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resultant residue was triturated with diethyl ether
  6. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5332521f85cb41eaaf7bc9d0707d3299
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697708B2

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