Hydrochloric Acid → 3-Bromo-5-methylimidazo[1,2-a]pyridine-2-carboxylic acid hydrochloride

HRID 1478679

Reaktionsgleichung

Reaktionsgleichung von HRID 1478679
[Br:1][C:2]1[N:6]2[C:7]([CH3:11])=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:12]([O:14]CC)=[O:13].[OH-].[Na+].[ClH:19]>C(O)C.O1CCCC1>[ClH:19].[Br:1][C:2]1[N:6]2[C:7]([CH3:11])=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:12]([OH:14])=[O:13]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58379339Ethyl 3-bromo-5-methylimidazo[1,2-a]pyridine-2-carboxylate

Produkt 1

HCID 672575653-Bromo-5-methylimidazo[1,2-a]pyridine-2-carboxylic acid hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of ethyl 3-bromo-5-methylimidazo[1,2-a]pyridine-2-carboxylate (0.62 g, 2.2 mmol) in ethanol (3.3 mL) and tetrahydrofuran (3.3 mL) was treated with 1 M sodium hydroxide (6.5 mL, 6.5 mmol) and stirred at 20° C. for 2 h. The reaction mixture was concentrated and the resultant solid was diluted with water, cooled to 0° C., and treated with 1 M hydrogen chloride (8.7 mL, 8.7 mmol) dropwise. The aqueous mixture was concentrated to a solid that was diluted with acetonitrile and reconcentrated (2×) to give the desired product which contained sodium chloride. This material was used without further purification. LCMS for C9H8BrN2O2 (M+H)+: m/z=255.0, 257.0.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additionthe resultant solid was diluted with water
  3. temperaturecooled to 0° C.
  4. concentrationThe aqueous mixture was concentrated to a solid
  5. additionthat was diluted with acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-b0d03c54a1c24aa497bf8561771b2e6d
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403847B2

Verknüpfte Notizen

Wird geladen…