Réaction #2186196

ord-7bf38d6564274c56ade1ccc0df8fc41b

Équation de réaction

O=Cc1cc2c(cc1O)N(CCF)CCC2
1-(2-Fluoro-ethyl)-7-hydroxy-1,2,3,4-tetrahydro-quinoline-6-carbaldehyde
COC(=O)Cc1cn2cc(Cl)ccc2n1
(6-chloro-imidazo[1,2-a]pyridin-2-yl)-acetic acid methyl ester
C1CCNCC1
piperidine
O=c1oc2cc3c(cc2cc1-c1cn2cc(Cl)ccc2n1)CCCN3CCF
desired product
Rendement 67.4%
O=c1oc2cc3c(cc2cc1-c1cn2cc(Cl)ccc2n1)CCCN3CCF
3-(6-Chloro-imidazo[1,2-a]pyridin-2-yl)-8-(2-fluoro-ethyl)-5,6,7,8-tetrahydro-1-oxa-8-aza-anthracen-2-one
Rendement 67.4%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températurerefluxed for 18 h
  2. 2
    Autreto reach room temperature
  3. 3
    Filtrationthe precipitate filtered
  4. 4
    Lavagewashed with acetonitrile
  5. 5
    Autredried under high vacuum

Mode opératoire

200 mg (0.896 mmol) 1-(2-Fluoro-ethyl)-7-hydroxy-1,2,3,4-tetrahydro-quinoline-6-carbaldehyde and 201 mg (1 eq.) (6-chloro-imidazo[1,2-a]pyridin-2-yl)-acetic acid methyl ester in 6 mL benzene and 3 mL acetonitrile are treated with 0.177 mL (2 eq.) piperidine and refluxed for 18 h. The reaction mixture is allowed to reach room temperature and the precipitate filtered, washed with acetonitrile and dried under high vacuum to yield 240 mg (67%) of desired product as a yellow powder.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07569337B2uspto-grants-2009_08