Dichloromethane → tert-butyl (2S,4S)-4-methyl-2-[5-[4-(2-trimethylsilylethynyl)phenyl]-1H-benzimidazol-2-yl]pyrrolidine-1-carboxylate

HRID 1625515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1625515
[C:1]([Si:3]([CH3:6])([CH3:5])[CH3:4])#[CH:2].Br[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:35]=[CH:34][C:17]3[NH:18][C:19]([C@@H:21]4[CH2:25][C@H:24]([CH3:26])[CH2:23][N:22]4[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[N:20][C:16]=3[CH:15]=2)=[CH:10][CH:9]=1.C(Cl)Cl>[Cu]I.CN(C=O)C>[CH3:26][C@@H:24]1[CH2:23][N:22]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@H:21]([C:19]2[NH:18][C:17]3[CH:34]=[CH:35][C:14]([C:11]4[CH:12]=[CH:13][C:8]([C:2]#[C:1][Si:3]([CH3:6])([CH3:5])[CH3:4])=[CH:9][CH:10]=4)=[CH:15][C:16]=3[N:20]=2)[CH2:25]1

Komponenten

6

Edukt 3

HCID 6344DichloromethaneHCID 66111TrimethylsilylacetyleneHCID 178461439HCID 178461439, Verbindung

Produkt 1

HCID 178461440tert-butyl (2S,4S)-4-methyl-2-[5-[4-(2-trimethylsilylethynyl)phenyl]-1H-benzimidazol-2-yl]pyrrolidine-1-carboxylateAusbeute 48,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Ethynyl-trimethyl-silane (34.44 mg, 49.55 μL, 0.3506 mmol), tert-butyl (2S,4S)-2-[5-(4-bromophenyl)-1H-benzimidazol-2-yl]-4-methyl-pyrrolidine-1-carboxylate (80 mg, 0.1753 mmol), Pd(DPPF)(Cl)2.CH2Cl2(14.32 mg, 0.01753 mmol), TEA (35.48 mg, 48.87 μL, 0.3506 mmol) and CuI (3.339 mg, 0.01753 mmol) are dissolved to dry DMF (2 mL). The mixture is stirred at 70° C. under N2 overnight. After removal of the solvent under reduced pressure, the residue is purified by flash column chromatography on silica gel SP1 25M using methanol/CH2Cl2 (0-5%) in 20 cv to provide tert-butyl (2S,4S)-4-methyl-2-[5-[4-(2-trimethylsilylethynyl)phenyl]-1H-benzimidazol-2-yl]pyrrolidine-1-carboxylate (40 mg).

Aufarbeitung

  1. customAfter removal of the solvent under reduced pressure
  2. customthe residue is purified by flash column chromatography on silica gel SP1 25M

Quellen und Nachweise

ORD-Eintrag
ord-fc3ddfb0effd42498287c542789619cc
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08779156B2

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