Sodium Chloride → {4-[1-(4-Fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methyl-(2-methyl-pyrimidin-4-yl)-amine

HRID 1633714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633714
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][CH3:23])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.Cl[C:34]1[CH:39]=[CH:38][N:37]=[C:36]([CH3:40])[N:35]=1.[Na+].[Cl-]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH3:23])[C:34]4[CH:39]=[CH:38][N:37]=[C:36]([CH3:40])[N:35]=4)=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 81531DiisopropylethylamineHCID 4244474-Chloro-2-methylpyrimidineHCID 18679487{4-[1-(4-Fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methylamine

Produkt 1

HCID 18679566{4-[1-(4-Fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methyl-(2-methyl-pyrimidin-4-yl)-amineAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

20 mg (0.064 mmol) {4-[1-(4-Fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methylamine and 0.16 ml (0.96 mmol) N,N-diisopropyl ethyl amine in 1 ml of DMF were treated with 41 mg (0.32 mmol) 4-chloro-2-methylpyrimidine and stirred at 100° C. during 2 hours. After cooling to room temperature the mixture was treated with saturated aqueous NaCl and extracted three times with Et2O. Drying of the combined organic layers over Na2SO4, evaporation of the solvent and column chromatography on silica gel with EtOAc gave 19 mg (73%) {4-[1-(4-Fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methyl-(2-methyl-pyrimidin-4-yl)-amine as a light yellow oil, MS: 405 (MH+).

Aufarbeitung

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionextracted three times with Et2O
  3. dry with materialDrying of the combined organic layers over Na2SO4, evaporation of the solvent and column chromatography on silica gel with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-e0519721f87541c1a968fdb9b4b9485a
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06503907B2

Notizen zur Reaktion

Wird geladen…