Hydrochloric Acid → HCID 117778902, Verbindung

HRID 1526991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1526991
[CH3:1][C:2]1[N:10]([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:19]([O:21]C)=[O:20].[OH-].[Li+].Cl>CO.O>[CH3:1][C:2]1[N:10]([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:19]([OH:21])=[O:20]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 89740370HCID 89740370, Verbindung

Produkt 1

HCID 117778902HCID 117778902, VerbindungAusbeute 26,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-methyl-1-(1-phenylethyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylate (80 mg, 0.27 mmol) in methanol (3 mL) and water (1 mL) was added lithium hydroxide (57 mg, 1.36 mmol). The reaction mixture was stirred with refluxing for 15 hours. The mixture was adjusted pH 3 with 1N aqueous hydrochloric acid. The aqueous phase was extracted with dichloromethane (50 mL×3). The organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to give a residue, which was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give 2-methyl-1-(1-phenylethyl)-1H-pyrrolo-[3,2-b]pyridine-3-carboxylic acid (20 mg, 26%). LRMS (M−H+) m/z: calcd 279.12. found 279.

Aufarbeitung

  1. temperaturewith refluxing for 15 hours
  2. extractionThe aqueous phase was extracted with dichloromethane (50 mL×3)
  3. washThe organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue, which
  8. customwas purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-dfa89d70a1fb4e949e1d0a15d4a85247
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085583B2

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