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Hydrochloric Acid → 6-[5-(5-chloro-6-isopropoxy-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-1H-indole-3-carbaldehyde

HRID 1512805
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1512805
[C:1](Cl)(C(Cl)=O)=[O:2].[Cl:7][C:8]1[CH:9]=[C:10]([C:18]2[O:22][N:21]=[C:20]([C:23]3[CH:31]=[C:30]4[C:26]([CH:27]=[CH:28][NH:29]4)=[CH:25][CH:24]=3)[N:19]=2)[CH:11]=[N:12][C:13]=1[O:14][CH:15]([CH3:17])[CH3:16].Cl.[OH-].[Na+]>C(Cl)Cl.O.CN(C=O)C>[Cl:7][C:8]1[CH:9]=[C:10]([C:18]2[O:22][N:21]=[C:20]([C:23]3[CH:31]=[C:30]4[C:26]([C:27]([CH:1]=[O:2])=[CH:28][NH:29]4)=[CH:25][CH:24]=3)[N:19]=2)[CH:11]=[N:12][C:13]=1[O:14][CH:15]([CH3:17])[CH3:16]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 591460766-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indole

Produkt 1

HCID 591461746-[5-(5-chloro-6-isopropoxy-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-1H-indole-3-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

DMF (0.28 mL) was added dropwise to a solution of (COCl)2 (0.31 mL) in DCM (9 mL) at 0° C. The resulting mixture was stirred at 0° C. for 1 hour. Then a solution of 6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indole (D101) (1.06 g) in DCM (30 mL) was added. The reaction mixture was warmed to RT and stirred overnight. Then water and 2 M HCl was added. After stirred for 2 hours, the mixture was neutralized with 2 M aqueous NaOH solution until pH was between 8 and 9. The organic layer was separated and washed with brine, dried over anhydrous sodium sulfate. The dried solution was concentrated. The residue was purified by column chromatography to afford 6-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indole-3-carbaldehyde (D102) (620 mg) as a yellow solid. δH (DMSO-d6, 400 MHz): 1.46 (6H, d), 5.51 (1H, m), 7.99 (1H, d), 8.14 (1H, d), 8.30 (1H, s), 8.42 (1H, d), 8.46 (1H, d), 8.90 (1H, d), 8.98 (1H, br s), 10.12 (1H, d).

Aufarbeitung

  1. temperatureThe reaction mixture was warmed to RT
  2. stirringstirred overnight
  3. stirringAfter stirred for 2 hours
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe dried solution was concentrated
  8. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-50811fdbfcb3487ca7d9e6f747011697
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08217028B2

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