Diisopropylethylamine → 5-biphenyl-4-yl-6-chloro-2-(methylsulfonyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazole

HRID 340767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 340767
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:19]([Cl:20])=[CH:18][C:10]3[NH:11][C:12]([S:14]([CH3:17])(=[O:16])=[O:15])=[N:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[CH3:36][Si:37]([CH2:40][CH2:41][O:42][CH2:43]Cl)([CH3:39])[CH3:38]>C1COCC1.CCOC(C)=O>[C:1]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:19]([Cl:20])=[CH:18][C:10]3[N:11]([CH2:43][O:42][CH2:41][CH2:40][Si:37]([CH3:39])([CH3:38])[CH3:36])[C:12]([S:14]([CH3:17])(=[O:15])=[O:16])=[N:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 684868865-biphenyl-4-yl-6-chloro-2-(methylsulfonyl)-1H-benzimidazole

Produkt 1

HCID 583871305-biphenyl-4-yl-6-chloro-2-(methylsulfonyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5-biphenyl-4-yl-6-chloro-2-(methylsulfonyl)-1H-benzimidazole (5.37 g, 14.0 mmol) in THF (70 mL) was added DIPEA (3.67 mL, 21.0 mmol) followed by SEMCl (3.7 mL, 21.0 mmol). The reaction was maintained for 5 h at ambient temperature. Then the reaction mixture was diluted with EtOAc and washed with saturated aqueous NaHCO3, followed by brine. The organic phase was dried over Na2SO4, filtered, and concentrated. Chromatography of the resulting residue over silica eluting with 5-25% EtOAc/hexanes afforded the desired product as a white solid. LC-MS: calculated for C14H20ClN2O3SSi 485.97, observed m/e 428.83 (M+H)+ (Rt 2.30 min).

Aufarbeitung

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6238e7b8a5e4458f9a7b58f8f0b4211d
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895596B2

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