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

HRID 1054760

Reaktionsgleichung

Reaktionsgleichung von HRID 1054760
[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-57ca515a1c2d4a23a14ae3dff608bb0f
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394285B2

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