Chloride → HCID 67313333, Verbindung

HRID 1010702Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1010702
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:12](Cl)=[N:13][OH:14].[Cl:16][C:17]1[CH:18]=[C:19]([C:23]#[C:24][C:25]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[O:26])[CH:20]=[CH:21][CH:22]=1.N1C=CC=C(C=O)C=1.I(C1C=CC=CC=1C(O)=O)=O.C(=O)(O)[O-].[Na+].[Cl-]>C(O)(C)C.CCOCC>[Cl:16][C:17]1[CH:18]=[C:19]([C:23]2[O:14][N:13]=[C:12]([C:3]3[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=3[F:1])[C:24]=2[C:25]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[O:26])[CH:20]=[CH:21][CH:22]=1

Komponenten

9

Edukt 6

HCID 312ChlorideHCID 103713-PyridinecarboxaldehydeHCID 675372-Iodosylbenzoic acidHCID 516892Sodium Bicarbonate2×HCID 67314987HCID 67314987, VerbindungHCID 86229620HCID 86229620, Verbindung

Produkt 1

HCID 67313333HCID 67313333, VerbindungAusbeute 61,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A mixture of 60 mg (0.25 mmol) of 2-fluoro-5-trifluoromethyl-N-hydroxybenzenecarbox-imidoyl chloride, 50 mg (0.21 mmol) of 3-(3-chlorophenyl) 1-(3-pyridyl)-2-propyn-1-one (prepared similarly to procedures noted above from lithio 3-chlorophenylacetylide and 3-pyridinecarboxaldehyde, followed by IBX oxidation), and 26 mg (0.36 mmol) of sodium bicarbonate in 2.5 mL of isopropyl alcohol was heated at 55° C. overnight with shaking. An additional 30 mg of carboximidoyl chloride and 15 mg of sodium bicarbonate were added, and the reaction was heated for another 24 hrs. The mixture was cooled and diluted with ether. The ether fraction was washed with saturated sodium chloride and dried over magnesium sulfate. The drying agent was filtered off, and solvent was removed by rotoevaporation. The residue was purified by prepTLC to give 56 mg (0.13 mmol) of 5-(3-chlorophenyl)-3-(2-fluoro-5-trifluoromethylphenyl)-4-[(3-pyridyl)carbonyl]isoxazole. 1H NMR (CDCl3): δ 7.10 (t, 1), 7.41 (m, 1), 7.52 (m, 1), 8.65 (br s, 1), and 8.86 ppm (br s, 1). MS m/z: 447.0 (M+H).

Aufarbeitung

  1. customprepared similarly to procedures
  2. temperaturethe reaction was heated for another 24 hrs
  3. temperatureThe mixture was cooled
  4. washThe ether fraction was washed with saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe drying agent was filtered off
  7. customsolvent was removed by rotoevaporation
  8. customThe residue was purified by prepTLC

Quellen und Nachweise

ORD-Eintrag
ord-8297fecd97474d44b1e006ce294edba7
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977341B2

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