Hydrochloric Acid → 3-(4-Trifluoromethylsulfanyl-phenylamino)-isonicotinic acid

HRID 39601

Reaktionsgleichung

Reaktionsgleichung von HRID 39601
F[C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:11][C:12]([F:22])([F:21])[S:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl>C1COCC1>[F:11][C:12]([S:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:2]2[CH:10]=[N:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:16][CH:15]=1)([F:22])[F:21]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1230544-((Trifluoromethyl)thio)anilineHCID 3453613-Fluoropyridine-4-carboxylic acidHCID 2733832Lithium Hexamethyldisilazide

Produkt 1

HCID 576496423-(4-Trifluoromethylsulfanyl-phenylamino)-isonicotinic acidAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

3-Fluoro-isonicotinic acid (50 mg, 0.354 mmol) and 4-(trifluoromethylthio)aniline (68.5 mg, 0.354 mmol) was added to 2 ml dry THF and the mixture was cooled to −78° C. LiHMDS (1M in THF, 1.24 ml) was added and the mixture was allowed to warm to room temperature over night. Hydrochloric acid (1M in methanol, 5 ml) was added and the volatiles were removed in vacuo. The crude material was purified by preparative HPLC to give 11.4 mg (45 μmol; 10% yield) of pure desired product.

Aufarbeitung

  1. temperatureto warm to room temperature over night
  2. customthe volatiles were removed in vacuo
  3. customThe crude material was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-8f5710e49fab499ba4436d27471f746e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524911B2

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