Reaktion #1917243

Reaktionsgleichung

triethylamine

2-chloro-2′-chloro-5-methoxy-[1,1′-biphenyl]-4-carboxylic acid

2-Chloro-2′-chloro-5-methoxy-[1,1′-biphenyl]-4-carboxylic acid

thionyl chloride

10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

→

title compound

Ausbeute 54.0%

10-{[2′,6-Dichloro-3-methoxy-[1,1′-biphenyl]-4-yl]carbonyl}-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Ausbeute 54.0%

Lösungsmittel

dichloromethane

tetrahydrofuran

N,N-dimethylformamide

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 2 hours
2. 2
   Waschenwashed with saturated aqueous sodium bicarbonate and brine
3. 3
   TrocknenThe organic layer was dried over anhydrous magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated to dryness

Vorschrift

A stirred solution of the 2-chloro-2′-chloro-5-methoxy-[1,1′-biphenyl]-4-carboxylic acid of Step A (2.29 g, 7.71 mmol) in tetrahydrofuran (20 mL) containing a catalytic amount of N,N-dimethylformamide was treated dropwise with thionyl chloride (1.00 g, 8.48 mmol). The reaction mixture was stirred for 2 hours, and then added dropwise to a solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (1.42 g, 7.71 mmol) in tetrahydrofuran (20 mL) containing triethylamine (1.72 g, 16.96 mmol). The reaction mixture was stirred for 2 hours, diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness. Trituration of the residue with ethyl acetate provided 1.93 g of the title compound which was recrystallized from ethyl acetate/hexanes as white crystals, m.p. 209–211° C.

Quelle