Sodium Sulfite → 6-chloro-5-[4-(3-hydroxypropyl)phenyl]-1H-indole-3-carboxylic acid

HRID 338417Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338417
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][OH:22])=[CH:15][CH:14]=1.P([O-])(O)(O)=[O:24].[Na+].Cl([O-])=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>CC(=CC)C.C(O)(C)(C)C.O.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:24])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][OH:22])=[CH:15][CH:14]=1

Komponenten

7

Edukt 4

HCID 24437Sodium SulfiteHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 866987526-chloro-5-[4-(3-hydroxypropyl)phenyl]-1H-indole-3-carbaldehyde

Produkt 1

HCID 866987536-chloro-5-[4-(3-hydroxypropyl)phenyl]-1H-indole-3-carboxylic acidAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 230840282-Methyl-2-butene t-butanol waterLösungsmittel

Versuchsvorschrift

To 6-chloro-5-[4-(3-hydroxypropyl)phenyl]-1H-indole-3-carbaldehyde (40 mg, 0.13 mmol) in 2-methyl-2-butene/t-butanol/water (v/v/v=1/1/1, 6 mL) was added sodium dihydrogen phosphate (30.5 mg, 0.254 mmol) and sodium chlorite (23 mg, 0.25 mmol) at room temperature. The resulting mixture was stirred at room temperature for 14 hours. The reaction mixture was added sodium sulfite (0.254 mmol), diluted with water, extracted with EtOAc, then concentrated in vacuo and purified via preparative HPLC to give the title compound (6.0 mg, 14% yield).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. concentrationconcentrated in vacuo
  3. custompurified via preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d57b8685538e46dcb79054233b08a41f
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889730B2

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