Cesium carbonate → 2-[3-(3-Fluoro-4-morpholin-4-yl-piperidin-1-yl)-phenyl]-1-methyl-1H-benzoimidazole

HRID 2047406

Reaktionsgleichung

Reaktionsgleichung von HRID 2047406
[F:1][CH:2]1[CH:7]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][NH:4][CH2:3]1.Br[C:15]1[CH:16]=[C:17]([C:21]2[N:25]([CH3:26])[C:24]3[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=3[N:22]=2)[CH:18]=[CH:19][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][CH:2]1[CH:7]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[CH2:6][CH2:5][N:4]([C:15]2[CH:16]=[C:17]([C:21]3[N:25]([CH3:26])[C:24]4[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=4[N:22]=3)[CH:18]=[CH:19][CH:20]=2)[CH2:3]1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 9624512-(3-bromophenyl)-1-methyl-1H-benzimidazoleHCID 686707464-(3-Fluoro-piperidin-4-yl)-morpholine

Produkt 1

HCID 686713272-[3-(3-Fluoro-4-morpholin-4-yl-piperidin-1-yl)-phenyl]-1-methyl-1H-benzoimidazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

4-(3-Fluoro-piperidin-4-yl)-morpholine (0.085 g, 0.45 mmol), 2-(3-Bromo-phenyl)-1-methyl-1H-benzoimidazole (described in method N, step a, b) (0.10 g, 0.35 mmol), and cesium carbonate (10.50 g, 32.2 mmol) were placed into a dry sealed 7 mL vial under nitrogen and dry toluene (0.4 mL) was added. At the same time Palladium acetate (0.016 g, 0.07 mmol), and BINAP (0.065 g, 0.10 mmol) were placed into another dry sealed 7 mL vial under nitrogen and diluted with dry toluene (0.8 mL) After about 20 minutes the resulting suspension was added to the vial containing the starting materials.

Aufarbeitung

  1. additionwas added
  2. customsealed 7 mL vial under nitrogen
  3. additionwas added to the
  4. additionvial containing the starting materials

Quellen und Nachweise

ORD-Eintrag
ord-639d0b6d540e4f4bafe23bf639e62468
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592463B2

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