Reaktion #72819

Reaktionsgleichung

EtOAc

4-bromo-2-methyl-6-(4-morpholinyl)-1H-benzimidazole

potassium carbonate

1-(bromomethyl)-2-methyl-3-(trifluoromethyl)benzene

→

desired product

Ausbeute 70.0%

4-bromo-2-methyl-1-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-6-(4-morpholinyl)-1H-benzimidazole

Ausbeute 70.0%

Lösungsmittel

—

hexanes

N,N-Dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   Sonstigethe resulting reaction mixture
3. 3
   workup.STIRRINGwas stirred for 3 h at 80° C
4. 4
   TemperaturIt was then cooled to room temperature
5. 5
   FiltrationThe precipitate was collected by filtration
6. 6
   Waschenwashed with water
7. 7
   Trocknenfew mLs of hexanes and air dried

Vorschrift

A suspension of 4-bromo-2-methyl-6-(4-morpholinyl)-1H-benzimidazole, prepared as described in Example 62 (500 mg, 1.688 mmol) and potassium carbonate (700 mg, 5.06 mmol) in N,N-Dimethylformamide (DMF) (6 mL) was stirred at rt for 15 min. 1-(bromomethyl)-2-methyl-3-(trifluoromethyl)benzene (641 mg, 2.53 mmol) was added in and the resulting reaction mixture was stirred for 3 h at 80° C. It was then cooled to room temperature and poured into ice/water. The precipitate was collected by filtration, washed with water, then few mLs of hexanes and air dried. The crude material was purified on a silica gel column (ISCO, 0-80% EtOAc in hexanes) to the desired product (565 mg, 1.182 mmol, 70.0% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.59 (d, J=7.83 Hz, 1H), 7.16 (d, J=2.02 Hz, 1H), 7.10-7.15 (m, 1H), 6.46-6.52 (m, 2H), 5.25 (s, 2H), 3.75-3.89 (m, 4H), 3.05-3.14 (m, 4H), 2.55 (s, 3H), 2.51 (s, 3H). MS (ES+) m/e 468.9 [M+H]+.

Quelle