Réaction #1126959

Équation de réaction

water

2-chloro-N-[(3-fluorophenyl)-methyl]-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid amide

3-hydroxy-oxetane

KOtBu

→

N-[(3-Fluorophenyl)-methyl]-4-methyl-6-morpholin-4-yl-2-(oxetan-3-yloxy)-pyridine-3-carboxylic acid amide

Rendement 84.0%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   Autresynthesis
2. 2
   workup.ADDITIONwas added
3. 3
   Températurethe mixture was heated at 80° C. for 8 h
4. 4
   Extractionextracted with EtOAc
5. 5
   LavageThe organic layer was washed with water and brine
6. 6
   Séchagedried over Na2SO4
7. 7
   Concentrationconcentrated in vacuo
8. 8
   AutrePurification of the residue by CC (hexane/EtOAc 7:3)

Mode opératoire

A solution of 209 mg (2.82 mmol) 3-hydroxy-oxetane in THF (6 ml) was treated with 316 mg (2.81 mmol) KOtBu and was heated at 50° C. for 15 min. After cooling to RT a solution of 205 mg (0.56 mmol) 2-chloro-N-[(3-fluorophenyl)-methyl]-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid amide (synthesis is described in section a) of example 9) in THF (3 ml) was added and the mixture was heated at 80° C. for 8 h. The mixture was then poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 7:3) provided 190 mg (0.47 mmol, 84%) N-[(3-Fluorophenyl)-methyl]-4-methyl-6-morpholin-4-yl-2-(oxetan-3-yloxy)-pyridine-3-carboxylic acid amide (example 317). [M+H]+ 402.2.

Source