Potassium Carbonate → 3-[2-(4-Fluoro-phenyl)-pyridin-4-yl]-7-[3-(3-piperidin-1-yl-propoxy)-phenyl]-imidazo[1,2-a]pyridine

HRID 383276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 383276
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[N:18]4[CH:19]=[CH:20][C:21]([C:23]5[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=5)=[CH:22][C:17]4=[N:16][CH:15]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.Cl.Cl[CH2:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[N:18]4[CH:19]=[CH:20][C:21]([C:23]5[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:32][CH2:33][CH2:34][N:35]6[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]6)[CH:24]=5)=[CH:22][C:17]4=[N:16][CH:15]=3)[CH:11]=[CH:10][N:9]=2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 79624N-(3-chloropropyl)piperidine hydrochlorideHCID 68482795HCID 68482795, Verbindung

Produkt 1

HCID 252611023-[2-(4-Fluoro-phenyl)-pyridin-4-yl]-7-[3-(3-piperidin-1-yl-propoxy)-phenyl]-imidazo[1,2-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

3-{3-[2-(4-Fluoro-phenyl)-pyridin-4-yl]-imidazo[1,2-a]pyridin-7-yl}-phenol (Ex. 1.102) (1 eq, 0.131 mmol, 50 mg), 1-(3-chloropropyl)piperidine monohydrochloride (2.0 eq, 0.262 mmol, 53.7 mg) and potassium carbonate (3.0 eq, 0.394 mmol, 54.4 mg) are dissolved in DMF (4 ml) and heated at 60° C. for 16 h. The reaction mixture is diluted with CH2Cl2 and washed with NaHCO3 and brine. The organic phase is dried over MgSO4, filtered and evaporated to dryness. The reaction mixture is purified by flash chromatography on silica eluting with DCM/MeOH 7/3 to yield 3-[2-(4-fluoro-phenyl)-pyridin-4-yl]-7-[3-(3-piperidin-1-yl-propoxy)-phenyl]-imidazo[1,2-a]pyridine as a yellow solid; [M+H]+=507

Aufarbeitung

  1. washwashed with NaHCO3 and brine
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe reaction mixture is purified by flash chromatography on silica eluting with DCM/MeOH 7/3

Quellen und Nachweise

ORD-Eintrag
ord-98e5661756e741f09696a294b7a185f6
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367662B2

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