Article

Facile synthesis of 6-aryl 5-N-substituted pyridazinones: microwave-assisted Suzuki-Miyaura cross coupling of 6-chloropyridazinones.

GlaxoSmithKline Pharmaceuticals, 1250 South Collegeville Rd, Collegeville, Pennsylvania 19426, USA.
The Journal of Organic Chemistry (impact factor: 4.45). 09/2008; 73(18):7204-8. DOI:10.1021/jo801097v pp.7204-8
Source: PubMed

ABSTRACT A facile synthesis of 5-dialkylamino-6-aryl-(2H)-pyridazin-3-one from 5,6-dichloropyridazinone was carried out by using a palladium-catalyzed Suzuki-Miyaura cross coupling of 6-chloro-5-dialkylaminopyridazinone 1 with various arylboronic acids (3 equiv) as the key transformation. The Suzuki-Miyaura cross-coupling reaction proceeded smoothly under microwave irradiation at 135-140 degrees C for 30 min with 5 mol % of Pd catalyst in moderate to good isolated yields. The use of a CombiPhos Pd6 mixture catalyst system and a single Pd-SPhos catalyst system was evaluated.

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Keywords

CombiPhos Pd6 mixture catalyst system
 
coupling
 
facile synthesis
 
key transformation
 
microwave irradiation
 
Pd catalyst
 
single Pd-SPhos catalyst system
 
Suzuki-Miyaura cross-coupling reaction proceeded
 
various arylboronic acids