Two-step synthesis of 3-aryl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones

Synlett

Volumn , Issue 13, 2006, Pages 2083-2086

  Scott, Jeremy P ^a  

^a Merck Sharp & Dohme Limited   (United Kingdom)

Author keywords

Amination; Palladium; Ring closure; Tandem reaction

Indexed keywords

3 ARYL L,3 DIHYDRO 2H IMIDAZO[4,5 B]PYRIDIN 2 ONES; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; RING CLOSING METATHESIS; SYNTHESIS;

EID: 33748248999     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-947355     Document Type: Article

References (27)

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17. 2 was added a solution of 2-chloro-3-aminopyridine (40.9 g, 318 mmol) in THF (80 mL) over
18. +.
19. BINAP and dppf were found to be inferior for the formation of 2a than XantPhos.
20. First reported by van Leeuwen: Kranenberg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 1995, 14, 3081.
21. XantPhos = 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene.
22. 3 is employed as base. See: Ali, M. H.; Buchwald, S. L. J. Org. Chem. 2001, 66, 2560.
23. The THF used in our study had a water content between 60 mg/mL and 110 mg/mL as determined by Karl-Fischer titration. (15) The approach used in Scheme 2 for the construction of 3-phenyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one has not been previously reported and given the diversity of commercially available isocyanates, may constitute another general entry to compounds in this class.
24. All new compounds gave satisfactory spectroscopic characterisation data.
25. Alkylamines screened were cyclopropylamine, sec-butylamine, (R)-1-phenylethylamine and 1-(2-aminoethyl)-piperidine. In all instances <20A% of desired imidazopyridin-2-one was identified by LCMS using either THF or toluene-i-PrOH (4:1) as reaction solvent.
26. Use of a Josiphos ligand for amination of 2-chloropyridine with primary alkylamines has been recently reported: Shen, Q.; Shekhar, S.; Stambuli, J. P.; Hartwig, J. F. Angew. Chem. Int. Ed. 2005, 44, 1371.
27. 3/BINAP as catalyst system for amination.