Diisopropylethylamine → 2-Fluoro-N-methyl-N-(4-o-tolyl-pyridin-3-yl)-3-trifluoromethyl-benzamide

HRID 877965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877965
[F:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:15][NH:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29].CCN(C(C)C)C(C)C>C1COCC1>[F:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:16]([CH3:15])[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29])=[O:5]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27375592-Fluoro-3-(trifluoromethyl)benzoyl chlorideHCID 18403336N-methyl-4-o-tolylpyridin-3-amine

Produkt 1

HCID 601970952-Fluoro-N-methyl-N-(4-o-tolyl-pyridin-3-yl)-3-trifluoromethyl-benzamideAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Fluoro-3-trifluoromethylbenzoyl chloride (92 mg, 0.41 mmol, CAS RN 208173-19-7) was added to a solution of methyl-(4-o-tolyl-pyridin-3-yl)-amine (40 mg, 0.20 mmol, example 1, intermediate a) and DIPEA (70 μL, 0.40 mmol) in THF (1 mL). The reaction mixture was stirred overnight, filtered and all volatiles removed. The resulting oil was purified by flash chromatography on silica gel eluting with 33-50% EtOAc in n-hexane to yield the product as a waxy solid (65 mg, 83%). MS (ESI): m/z=470.0 [M+H]+.

Aufarbeitung

  1. filtrationfiltered
  2. customall volatiles removed
  3. customThe resulting oil was purified by flash chromatography on silica gel eluting with 33-50% EtOAc in n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-cdbdc46a06eb452ab03626406c542c50
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987307B2

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