Sodium Carbonate → 2-[5-(Dimethylamino)-2-methyl-3-oxo-2,3-dihydropyridazin-4-yl]benzaldehyde

4-Chloro-5-(dimethylamino)-2-methylpyridazin-3(2H)-one (50.00 mmol) was dissolved in dimethoxyethane (155 ml), and Pd(PPh3)4 (1.60 g, 1.38 mmol) was added under argon. After stirring at room temperature for 10 min, 2-formylbenzeneboronic acid (10.50 g, 70.00 mmol) and 2M Na2CO3 solution (49.5 ml) were added. Subsequently, the reaction mixture was refluxed (oil bath temperature: 110° C.) for 15 h. The reaction was followed by TLC (eluent: chloroform:acetone (9:1)). Upon cooling the reaction mixture was poured onto ice (375 g), filtered over Celite and washed with chloroform (130 ml). The two layers were separated and the aqueous phase was extracted with chloroform (3×380 ml). The combined organic layers were washed with water (1×100 ml), dried over MgSO4, filtered and purified by flash column chromatography with a mixture of diisopropyl ether and acetone (8:1) as the eluent and crystallized from a mixture of ethyl acetate and hexane (2.3:1).

1. temperatureSubsequently, the reaction mixture was refluxed (oil bath temperature: 110° C.) for 15 h
2. temperatureUpon cooling the reaction mixture
3. additionwas poured onto ice (375 g)
4. filtrationfiltered over Celite
5. washwashed with chloroform (130 ml)
6. customThe two layers were separated
7. extractionthe aqueous phase was extracted with chloroform (3×380 ml)
8. washThe combined organic layers were washed with water (1×100 ml)
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. custompurified by flash column chromatography with a mixture of diisopropyl ether and acetone (8:1) as the eluent
12. customcrystallized from a mixture of ethyl acetate and hexane (2.3:1)

ORD-Eintrag

ord-aeffc808ff7e4f3fb6110e79463d53f0

Quelldatensatz

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08536210B2