Reaction #2186196

Reaction equation

1-(2-Fluoro-ethyl)-7-hydroxy-1,2,3,4-tetrahydro-quinoline-6-carbaldehyde

(6-chloro-imidazo[1,2-a]pyridin-2-yl)-acetic acid methyl ester

piperidine

→

desired product

Yield 67.4%

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

Yield 67.4%

Solvents

benzene

acetonitrile

Conditions

Workup

1. 1
   Temperaturerefluxed for 18 h
2. 2
   Otherto reach room temperature
3. 3
   Filtrationthe precipitate filtered
4. 4
   Washwashed with acetonitrile
5. 5
   Otherdried under high vacuum

Procedure

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