3-Amino-4-chloropyridine → HCID 25211384, Verbindung

HRID 572292

Reaktionsgleichung

Reaktionsgleichung von HRID 572292
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:9][C:10]1[C:11]([C:19]2[S:23][C:22]([C:24](Cl)=[O:25])=[CH:21][CH:20]=2)=[N:12][O:13][C:14]=1[C:15]([F:18])([F:17])[F:16]>C1COCC1>[Cl:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:1][C:24]([C:22]1[S:23][C:19]([C:11]2[C:10]([CH3:9])=[C:14]([C:15]([F:17])([F:18])[F:16])[O:13][N:12]=2)=[CH:20][CH:21]=1)=[O:25]

Komponenten

4

Edukt 2

HCID 5819323-Amino-4-chloropyridineHCID 86628351HCID 86628351, Verbindung

Produkt 1

HCID 25211384HCID 25211384, VerbindungAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3-amino-4-chloropyridine (129 mg, 1.0 mmol) in THF (2 mL) was treated with solid 5-(4-methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carbonyl chloride (148 mg, 0.5 mmol, as prepared in Example 2 Method B) and allowed to stir for 1 hr. The reaction was then evaporated and the residue chromatographed on silica gel with EtOAc/hexanes (70%) as eluant to afford product as a colorless solid (31 mg, 16%). 1H NMR (CDCl3) 2.39 (d, J=1.5, 3H), 7.39 (d, J=5.3, 1H), 7.56 (d, J=7.56, 4.1, 1H), 7.72 (d, J=4.1, 1H), 8.22 (s, 1H), 8.33 (d, J=4.7, 1H), 9.61 (s, 1H). 13C NMR 8.0, 114.8, 118.7 (q, J=271), 129.0, 129, 7, 132.9, 134.6, 140.5, 143.8, 146.1, 157.7, 159.0, 19F NMR −63.1. LC/MS 6.34 min, [M+1]+ 388.

Aufarbeitung

  1. customThe reaction was then evaporated
  2. customthe residue chromatographed on silica gel with EtOAc/hexanes (70%) as eluant

Quellen und Nachweise

ORD-Eintrag
ord-65632bb6ba0c4b71b49af4f9368c64c8
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029397B2

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