Reaktion #88516

Reaktionsgleichung

6′-chloro-2,5′-difluoro-[3,4′]bipyridinyl-3′-ylamine

sodium bis(trimethylsilyl)amide

→

title compound

Ausbeute 64.0%

6-Chloro-5-fluoro-9H-dipyrido[2,3-b;4′3′-d]pyrrole

Ausbeute 64.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONWhen the addition
2. 2
   SonstigeThe bulk of the solvent was evaporated in-vacuo
3. 3
   workup.ADDITIONthe residue poured into ice-cold 1N hydrochloric acid
4. 4
   FiltrationThe resulting slurry was filtered
5. 5
   Waschenthe solid washed with water
6. 6
   SonstigeThe filter cake was collected
7. 7
   Sonstigetriturated with acetone

Vorschrift

A solution of 6′-chloro-2,5′-difluoro-[3,4′]bipyridinyl-3′-ylamine (70 g, 290 mmol) in THF (300 mL) was added dropwise to a solution of sodium bis(trimethylsilyl)amide (720 mL, 1M in THF, 720 mmol) at such a rate that the reaction temperature was maintained at 40° C. When the addition was complete the mixture was stirred for ca. 1 hour at ambient temperature. The bulk of the solvent was evaporated in-vacuo and the residue poured into ice-cold 1N hydrochloric acid. The resulting slurry was filtered and the solid washed with water. The filter cake was collected and triturated with acetone followed by diethyl ether to afford the title compound as a beige solid (40.9 g, 64%). The trituration liquors were evaporated and the residue triturated with methanol followed by diethyl ether to afford a second crop of title compound as a brown solid (6.1 g, 10%). Total yield=47 g, 74%. 1H NMR (400 MHz, DMSO-d6): 13.24 (s, 1H), 8.91 (d, J=2.5 Hz, 1H), 8.77 (dd, J=4.8, 1.7 Hz, 1H), 8.65 (dd, J=7.9, 1.7 Hz, 1H), 7.50 (dd, J=7.9, 4.8 Hz, 1H).

Quelle