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

HRID 1054786Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1054786
[NH:1]1[CH2:4][CH:3]([C:5]2[CH:10]=[CH:9][C:8]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][C:19]=3[Cl:20])[NH:16][CH:15]=[C:14]4[CH:21]=[O:22])=[CH:7][CH:6]=2)[CH2:2]1.P([O-])(O)(O)=[O:24].[Na+].Cl([O-])=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>CC(=CC)C.CC(O)(C)C.O>[NH:1]1[CH2:4][CH:3]([C:5]2[CH:10]=[CH:9][C:8]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][C:19]=3[Cl:20])[NH:16][CH:15]=[C:14]4[C:21]([OH:24])=[O:22])=[CH:7][CH:6]=2)[CH2:2]1

Komponenten

6

Edukt 4

HCID 24437Sodium SulfiteHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 866987735-[4-(azetidin-3-yl)phenyl]-6-chloro-1H-indole-3-carbaldehyde

Produkt 1

HCID 866987745-[4-(azetidin-3-yl)phenyl]-6-chloro-1H-indole-3-carboxylic acidAusbeute 10,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

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

Versuchsvorschrift

To 5-[4-(azetidin-3-yl)phenyl]-6-chloro-1H-indole-3-carbaldehyde (94 mg, 0.30 mmol) in 2-methyl-2-butene/t-BuOH/H2O (v/v/v=1/1/1, 4 mL) was added sodium dihydrogen phosphate (364 mg, 3.04 mmol) and sodium chlorite (274 mg, 3.04 mmol) at room temperature. The resulting mixture was stirred at room temperature for 24 hours. To the reaction mixture was added sodium sulfite (383 mg, 3.04 mmol), then concentrated in vacuo and purified via reverse phase HPLC to give the title compound (10 mg, 10% yield). 1H NMR (400 MHz, CD3OD) δ 8.03-80.4 (d, 2 H), 7.62 (s, 1 H), 7.48-7.52 (m, 4 H), 4.44-4.48 (m, 2 H), 4.32-4.34 (m, 3 H).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. custompurified via reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-4acf7e2388934e91ba3ebdd460d31c8d
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394285B2

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