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

HRID 338443Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338443
[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, 2H), 7.62 (s, 1H), 7.48-7.52 (m, 4H), 4.44-4.48 (m, 2H), 4.32-4.34 (m, 3H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-f9d2e966535044ffb724f3d65b9250c3
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889730B2

Notizen zur Reaktion

Wird geladen…