Reaktion #805878

Reaktionsgleichung

Compound 74a

8-Morpholino-3-phenylimidazo[1,2-b]pyridazine-2-carbaldehyde

compound 73d

Ethyl-2-[(diethoxyphosphoryl]methyl)quinoline-5-carboxylate

NaH

→

compound 74b

(E)-2-(2-(8-Morpholino-3-phenylimidazo[1,2-b]pyridazin-2-yl)vinyl)quinoline-5-carboxylic acid

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to rt
2. 2
   Sonstigequenched with saturated sodium bicarbonate (2 mL)
3. 3
   Extraktionextracted with DCM (10 mL)
4. 4
   SonstigeThe DCM layer was separated
5. 5
   Trocknendried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   Sonstigethe resultant residue was purified by flash column chromatography over silica gel (0-100% EtOAc/DCM)

Vorschrift

A solution of compound 73d (119 mg, 0.339 mmol) in THF (6 mL) was treated with NaH (36.9 mg, 0.924 mmol) at 0° C. and the resulting mixture was allowed to warm to room temperature over 10 min. Compound 74a (95.0 mg, 0.308 mmol) was then added in one portion and the resultant mixture was heated to 55° C. for 1 h. The reaction was allowed to cool to rt, quenched with saturated sodium bicarbonate (2 mL) and extracted with DCM (10 mL). The DCM layer was separated, dried over Na2SO4, filtered, and concentrated, and the resultant residue was purified by flash column chromatography over silica gel (0-100% EtOAc/DCM) to afford compound 74b. Mass spectrum (LCMS, ESI pos.) Calcd. For C28H23N5O3 478.2 (M+H). found 478.1.

Quelle