Reaktion #805862

Reaktionsgleichung

imidazole

compound 5f

tert-Butyl 4-(2-formyl-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)benzoate

2-methylquinolin-4-ol

TMSCl

→

compound 64a

(E)-tert-Butyl 4-(2-(2-(4-hydroxyquinolin-2-yl)vinyl)-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)benzoate

Lösungsmittel

DMF

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to rt
2. 2
   Waschenwashed with water (3×20 mL) and brine (15 mL)
3. 3
   SonstigeThe solvent was removed in vacuo
4. 4
   workup.ADDITIONthe residue was treated with DCM (5 mL)
5. 5
   Sonstigewas purified by flash column chromatography on silica gel (0:1-1:19 MeOH/DCM)

Vorschrift

To a mixture of compound 5f (150 mg, 0.367 mmol) and 2-methylquinolin-4-ol (292 mg, 1.84 mmol) in 4 mL of DMF was added TMSCl (469 μL, 3.67 mmol) dropwise. The resulting mixture was stirred at 90° C. for 16 h. After cooling to rt, the mixture was treated with 60 mL of EtOAc and washed with water (3×20 mL) and brine (15 mL). The solvent was removed in vacuo and the residue was treated with DCM (5 mL). To this mixture was added imidazole (50.0 mg, 0.734 mmol), and the resulting mixture turned clear and was purified by flash column chromatography on silica gel (0:1-1:19 MeOH/DCM) to afford compound 64a as a yellow solid. 1H-NMR (CDCl3; 400 MHz) δ 11.97 (br. s., 1H), 8.26 (d, J=7.8 Hz, 1H), 7.88-8.03 (m, 3H), 7.43-7.83 (m, 6H), 7.22 (t, J=7.5 Hz, 1H), 6.49 (s, 1H), 6.03 (d, J=5.6 Hz, 1H), 3.94 (br. s., 4H), 3.82 (br. s., 4H), 1.55 (s, 9H). Mass spectrum (ESI, m/z): Calcd. for C32H31N5O4, 550.2 (M+H). found 550.5.

Quelle