Dimethyl Sulfide → (2,4-dimethylthiophen-3-yl)-3-(2-fluoro-4-hydroxyphenyl)-1-methyl-1H-pyrazole-5-carbonitrile

HRID 1410172Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1410172
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH3:24])[C:6]=1[C:7]1[C:8]([C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][C:16]=2[F:23])=[N:9][N:10]([CH3:14])[C:11]=1[C:12]#[N:13].S(C)C>C(Cl)Cl.B(F)(F)F>[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH3:24])[C:6]=1[C:7]1[C:8]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=2[F:23])=[N:9][N:10]([CH3:14])[C:11]=1[C:12]#[N:13]

Komponenten

5

Edukt 2

HCID 1068Dimethyl SulfideHCID 671200444-(2,4-dimethylthiophen-3-yl)-3-(2-fluoro-4-methoxyphenyl)-1-methyl-1H-pyrazole-5-carbonitrile

Produkt 1

HCID 136350247(2,4-dimethylthiophen-3-yl)-3-(2-fluoro-4-hydroxyphenyl)-1-methyl-1H-pyrazole-5-carbonitrileAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6356Boron trifluorideLösungsmittel

Versuchsvorschrift

4-(2,4-dimethylthiophen-3-yl)-3-(2-fluoro-4-methoxyphenyl)-1-methyl-1H-pyrazole-5-carbonitrile (17 mg, 0.05 mmol) was dissolved in dry DCM (2 mL) and BF3.Me2S (1 M solution in DCM, 0.3 mL, 0.3 mmol) was added and the mixture was stirred at room temperature over night. The mixture was concentrated and MeOH was added to quench the reaction The crude product was purified on silica gel to give -(2,4-dimethylthiophen-3-yl)-3-(2-fluoro-4-hydroxyphenyl)-1-methyl-1H-pyrazole-5-carbonitrile (7.0 mg, 43%).

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. additionMeOH was added
  3. customto quench
  4. customthe reaction The crude product
  5. customwas purified on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-7e5fe42755ca44b19b7e10f3a0f0482c
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921402B2

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