Hydrochloric Acid → 6-Chloro-2-(4-fluoroindolin-2-yl)pyridin-3-ol

HRID 1776849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1776849
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[C:14]([F:17])[CH:13]=[CH:12][CH:11]=3)[C:5]([OH:18])=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>CCO>[Cl:1][C:2]1[N:7]=[C:6]([CH:8]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[F:17])[NH:9]2)[C:5]([OH:18])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 867262926-chloro-2-(4-fluoro-1H-indol-2-yl)pyridin-3-ol

Produkt 1

HCID 867262936-Chloro-2-(4-fluoroindolin-2-yl)pyridin-3-olAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 6-chloro-2-(4-fluoro-1H-indol-2-yl)pyridin-3-ol (10 g, 38 mmol) and metal Sn (23 g, 190 mmol) in CH3CH2OH/con. HCl (60 mL/40 mL) was stirred under reflux for 3 hours. The mixture was cooled to room temperature and adjusted to pH=7 by saturated NaOH and filtered though a Celit pad. The filtrate was extracted with EtOAc, washed by brine, dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using silica gel chromatography (petroleum ether:EtOAc=10:1) to get 6-chloro-2-(4-fluoroindolin-2-yl)pyridin-3-ol (8 g, yield: 80%). 1H-NMR (CDCl3, 400 MHz) δ 9.86 (s, 1H), 7.10˜7.20 (m, 3H), 6.33˜6.91 (m, 2H), 5.15˜5.21 (m, 1H), 4.61 (s, 1H), 3.65˜3.71 (m, 1H), 3.04˜3.11 (m, 1H). MS (M+H)+: 265.

Aufarbeitung

  1. temperatureunder reflux for 3 hours
  2. filtrationfiltered though a Celit pad
  3. extractionThe filtrate was extracted with EtOAc
  4. washwashed by brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-807e9b9902d647359d27e99619788d9a
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09265773B2

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