Hydrochloric Acid → 8-Chloro-5-(3-fluorophenyl)imidazo[1,2-a]pyridine-6-carboxylic acid

HRID 717830Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 717830
[Cl:1][C:2]1[C:3]2[N:4]([CH:19]=[CH:20][N:21]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([C:8]([O:10]C)=[O:9])[CH:7]=1.[OH-].[Na+].O.Cl>O1CCCC1>[Cl:1][C:2]1[C:3]2[N:4]([CH:19]=[CH:20][N:21]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([C:8]([OH:10])=[O:9])[CH:7]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14798Sodium HydroxideHCID 58515952Methyl 8-chloro-5-(3-fluorophenyl)imidazo[1,2-a]pyridine-6-carboxylate

Produkt 1

HCID 669927768-Chloro-5-(3-fluorophenyl)imidazo[1,2-a]pyridine-6-carboxylic acidAusbeute 102,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of methyl 8-chloro-5-(3-fluorophenyl)imidazo[1,2-a]pyridine-6-carboxylate (0.18 g, 0.57 mmol) in tetrahydrofuran (3 mL) was treated with 1 M sodium hydroxide in water (1.7 mL, 1.7 mmol) and stirred at 20° C. for 6 hours. The reaction mixture was concentrated, diluted with water, cooled to 0° C., and treated with 1 M hydrogen chloride in water (2.3 mL, 2.3 mmol) dropwise. The resultant suspension was filtered to give the desired product (0.17 g, quantitative) that was used without further purification. LCMS calculated for C14H9ClFN2O2 (M+H)+: m/z=291.0. found: 290.9.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. temperaturecooled to 0° C.
  4. filtrationThe resultant suspension was filtered

Quellen und Nachweise

ORD-Eintrag
ord-91f554a5b32149e3960b2d0f3b75430b
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193721B2

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