Reaktion #805752

Reaktionsgleichung

compound 5e

8-Morpholinoimidazo[1,2-b]pyridazine-2-carbaldehyde

tert-butyl-4-bromobenzoate

triphenylphosphine

potassium acetate

→

compound 5f

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

Lösungsmittel

water

N,N-dimethylacetamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to rt
2. 2
   Extraktionextracted with EtOAc (2×100 mL)
3. 3
   WaschenThe combined organic layers were washed with brine
4. 4
   Trocknendried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe obtained residue was purified by flash chromatography on silica gel (10-60% EtOAc/heptane)

Vorschrift

To a mixture of compound 5e (0.57 g, 2.5 mmol), tert-butyl-4-bromobenzoate (0.97 g, 3.7 mmol), palladium acetate (38 mg, 0.17 mmol), triphenylphosphine (45 mg, 0.17 mmol) and potassium acetate (0.72 g, 7.3 mmol) were added while under an argon atmosphere and in dry N,N-dimethylacetamide (5 mL). The reaction mixture was stirred at 110° C. for 22 h, allowed to cool to rt, diluted with water (100 mL), and extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The obtained residue was purified by flash chromatography on silica gel (10-60% EtOAc/heptane) to give compound 5f as a pale yellow solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 10.13 (s, 1H), 8.13-8.21 (m, J=8.1 Hz, 2H), 8.09 (d, J=5.6 Hz, 1H), 7.85 (d, J=8.3 Hz, 2H), 6.15 (d, J=5.6 Hz, 1H), 4.02-4.14 (m, 4H), 3.90-4.00 (m, 4H), 1.62 (s, 9H).

Quelle