Potassium Iodide → HCID 21471843, Verbindung

HRID 1734059

Reaktionsgleichung

Reaktionsgleichung von HRID 1734059
[C:1]([N:4]1[CH2:9][CH2:8][C:7]2[C:10]([CH2:14][CH2:15]Br)=[C:11]([CH3:13])[S:12][C:6]=2[CH2:5]1)(=[O:3])[CH3:2].Cl.[F:18][C:19]1[CH:27]=[C:26]2[C:22]([C:23]([CH:35]3[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)=[N:24][N:25]2[C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.C1(C)C=CC=CC=1>[C:1]([N:4]1[CH2:9][CH2:8][C:7]2[C:10]([CH2:14][CH2:15][N:38]3[CH2:37][CH2:36][CH:35]([C:23]4[C:22]5[C:26](=[CH:27][C:19]([F:18])=[CH:20][CH:21]=5)[N:25]([C:28]5[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=5)[N:24]=4)[CH2:40][CH2:39]3)=[C:11]([CH3:13])[S:12][C:6]=2[CH2:5]1)(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 21471852HCID 21471852, VerbindungHCID 214719356-Acety-3-(2-bromoethyl)-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridine

Produkt 1

HCID 21471843HCID 21471843, VerbindungAusbeute 60,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 334 mg of 6-acetyl-3-(2-bromoethyl)-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridine, 420 mg of 4-(6-fluoro-1-(4-fluorophenyl)-1H-indazol-3-yl)piperidine hydrochloride, 500 mg of potassium carbonate and 216 mg of potassium iodide in 10 ml of dimethylformamide and 10 ml of toluene was stirred at 85° C. for 8 hours and concentrated in vacuo. To the residue were added ethyl acetate and water, and separated. The ethyl acetate layer was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on a silica gel to give 360 mg of 6-acetyl-3-(2-(4-(6-fluoro-1-(4-fluorophenyl)-1H-indazol-3-yl)piperidin-1-yl)ethyl)-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridine as an oil, m.p. 193°-196° C. as oxalate thereof.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additionTo the residue were added ethyl acetate and water
  3. customseparated
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on a silica gel

Quellen und Nachweise

ORD-Eintrag
ord-7ef1bce9e5f749ffb20f47a49e1db077
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05532240

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