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Potassium Iodide → HCID 10157486, Verbindung

HRID 966474
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 966474
[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][CH2:22]Cl)[CH:18]=2)[N:13]([CH3:24])[C:12]=1[CH3:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:34]([NH:36][CH2:37][CH3:38])[CH3:35].[K+].[Br-]>CN(C=O)C.O.CC#N>[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][CH2:22][N:36]([CH2:37][CH3:38])[CH2:34][CH3:35])[CH:18]=2)[N:13]([CH3:24])[C:12]=1[CH3:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 4875Potassium IodideHCID 8021Diethylamine2×HCID 11430Potassium CarbonateHCID 253877Potassium BromideHCID 23393870HCID 23393870, Verbindung

Produkt 1

HCID 10157486HCID 10157486, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 1-methyl-5-(2-chloro-ethoxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (0.576 mmol, 0.206 g, Example 8, Step A) in 5.76 mL of DMF was added potassium carbonate (0.576 mmol, 0.080 g), potassium iodide (0.0576 mmol, 0.010 g), and diethylamine (2.30 mmol, 0.238 mL, Aldrich). The mixture was heated at 100° C. for 20 hours, an additional 2.30 mmol of diethylamine was added and heating was continued for 21 hours. The solution was cooled to room temperature, diluted with water (10 mL), and extracted with ethyl acetate (4×15 mL). The combined extracts were washed with water (10 mL), saturated aqueous NaCl (10 mL), dried over MgSO4, and concentrated to a brown oil (0.234 g). The product was purified by silica gel flash column chromatography (5-10% MeOH/CH2Cl2) to give a tan solid (0.114 g, 50/o): mp 73-74° C.; IR (KBr) 2968, 2918, 1692, 1186, 1101 cm−1; 1HNMR (400 MHz, DMSO-d6) δ 0.92 (t, J=7.08 Hz, 6H, N(CH2CH3)2), 2.46-2.51 (m, 4H, 2 NCH2), 2.66 (s, 3H, ArCH3), 2.68-2.73 (m, 2H, NCH2), 3.65 (s, 3H, NCH3), 3.85 (t, J=6.11 Hz, 2H, CH2OAr), 5.28 (s, 2H, CO2CH2Ph), 6.75 (dd, J=8.79, 2.44 Hz, 1H, ArH), 7.28-7.32 (m, 1H, ArH), 7.35-7.39 (m, 4H, ArH), 7.46 (d, J=7.57 Hz, 2H, ArH); MS(APCI+): m/z 395.1 (M+1). HPLC (ALLTECH/ALLTIMA C-18,50:50-2:98H2O/CH3CN+0.05% TFA): retention time=3.617 min, 96.84% purity.

Aufarbeitung

  1. temperatureheating
  2. temperatureThe solution was cooled to room temperature
  3. extractionextracted with ethyl acetate (4×15 mL)
  4. washThe combined extracts were washed with water (10 mL), saturated aqueous NaCl (10 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to a brown oil (0.234 g)
  7. customThe product was purified by silica gel flash column chromatography (5-10% MeOH/CH2Cl2)
  8. customto give a tan solid (0.114 g, 50/o)

Quellen und Nachweise

ORD-Eintrag
ord-61289bda7cc94de69cf4e1c6ad1eb929
Quelldatensatz
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06951848B2

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