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

HRID 39602

Reaktionsgleichung

Reaktionsgleichung von HRID 39602
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])[O: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]([F:21])([F:22])[O:13][C:14]1[CH:15]=[CH:16][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:19][CH:20]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 3453613-Fluoropyridine-4-carboxylic acidHCID 6008484-(Trifluoromethoxy)anilineHCID 2733832Lithium Hexamethyldisilazide

Produkt 1

HCID 576496383-(4-Trifluoromethoxy-phenylamino)-isonicotinic acidAusbeute 9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

3-Fluoro-isonicotinic acid (50 mg, 0.354 mmol) and 4-(trifluoromethoxy)aniline (62.8 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 9.5 mg (32 μmol; 9% 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-68aa3eff66cc499abf1b2121278b6d86
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524911B2

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