Reaktion #72795

Reaktionsgleichung

N,2-dimethyl-N-(methyloxy)-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-1H-benzimidazole-4-carboxamide

methylmagnesium chloride

→

product

Ausbeute 62.6%

1-[2-methyl-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-1H-benzimidazol-4-yl]ethanone

Ausbeute 62.6%

Lösungsmittel

Tetrahydrofuran

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting reaction mixture
2. 2
   Sonstigequenched very carefully with saturated aqueous ammonium chloride
3. 3
   workup.ADDITIONThe mixture was diluted with ethyl acetate (50 mL)
4. 4
   Extraktionthe aqueous phase was extracted with ethyl acetate (50 mL×2)
5. 5
   WaschenThe combined organic phases were washed with brine (50 mL)
6. 6
   Trocknendried over (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   EinengenThe solution was concentrated under reduced pressure
9. 9
   SonstigeThe crude product was purified on a silica column (40˜60% EtOAc/Hexane)

Vorschrift

To a solution of N,2-dimethyl-N-(methyloxy)-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-1H-benzimidazole-4-carboxamide (82 mg, 0.184 mmol) in Tetrahydrofuran (THF) (10 mL) was added a 3.0 M solution of methylmagnesium chloride (0.123 mL, 0.369 mmol) in THF at 0° C. The resulting reaction mixture was stirred at 0° C. for 2 h and then quenched very carefully with saturated aqueous ammonium chloride. The mixture was diluted with ethyl acetate (50 mL) and the aqueous phase was extracted with ethyl acetate (50 mL×2). The combined organic phases were washed with brine (50 mL), dried over (MgSO4), and filtered. The solution was concentrated under reduced pressure. The crude product was purified on a silica column (40˜60% EtOAc/Hexane) to give the product (46 mg, 59%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.47 (s, 3H), 3.00 (s, 3H), 3.02-3.10 (m, 4H), 3.59-3.73 (m, 4H), 6.06 (s, 2H), 6.33 (d, J=6.82 Hz, 1H), 7.21-7.42 (m, 3H), 7.52-7.76 (m, 2H), 7.86 (d, J=8.34 Hz, 1H), 8.02 (d, J=7.33 Hz, 1H), 8.25 (d, 1H). MS (ES+) m/e 399.9[M+H]+.

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