Methyl iodide → HCID 58541893, Verbindung

HRID 1966734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1966734
[Br:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]3[N:16]=[N:17][NH:18][N:19]=3)=[N:8][C:4]=2[CH:3]=1.IC.[C:28]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]([C:20]([CH3:22])([CH3:21])[CH3:23])[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]3[N:16]=[N:17][N:18]([CH3:28])[N:19]=3)=[N:8][C:4]=2[CH:3]=1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58541950HCID 58541950, Verbindung

Produkt 1

HCID 58541893HCID 58541893, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a vial is added 5-bromo-1-tert-butyl-2-[2-(2H-tetrazol-5-yl)-phenyl]-1H-benzimidazole (158 mg, 0.4 mmol) in DMF (5 mL), followed by the addition of iodomethane (114 mg, 0.8 mmol) and K2CO3 (110 mg, 0.8 mmol). The reaction mixture is stirred at room temperature for 0.5 hour. The reaction mixture is diluted with EtOAc, washed with water then, brine, dried with Na2SO4, filtered and concentrated. The residue is loaded to a silica gel column. The column is eluted with 0-3% MeOH/CH2Cl2. The product fractions are collected and is concentrated to afford 5-bromo-1-tert-butyl-2-[2-(2-methyl-2H-tetrazol-5-yl)-phenyl]-1H-benzimidazole (62 mg, 38%). LCMS (ESMS): m/z 411.59, 413.47 (M++1)

Aufarbeitung

  1. washwashed with water
  2. dry with materialbrine, dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washThe column is eluted with 0-3% MeOH/CH2Cl2
  6. customThe product fractions are collected
  7. concentrationis concentrated

Quellen und Nachweise

ORD-Eintrag
ord-d2a3c07509164658b7a699539aa50083
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420655B2

Notizen zur Reaktion

Wird geladen…