Réaction #1841057

Équation de réaction

NH4Cl

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

iso-propyl-magnesium-chloride

→

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

Rendement 36.1%

Solvants

THF NMP

Conditions de réaction

Traitement

1. 1
   Températureto warm to 0° C. within 1 h
2. 2
   Extractionwas extracted with EtOAc (3×20 ml)
3. 3
   LavageThe combined organic layers were washed with water and brine
4. 4
   Séchagedried over Na2SO4
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutrePurification of the residue by CC (hexane/EtOAc 7:3)

Mode opératoire

A solution of 300 mg (0.83 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/NMP (6:1 v/v, 14 ml) was cooled to −30° C. At this temperature were successively added 58 mg (0.16 mmol) Fe(acac)3 and 6 ml (12.0 mmol, 2M in THF) iso-propyl-magnesium-chloride. The RM was then allowed to warm to 0° C. within 1 h. Then sat. aq. NH4Cl sol. was added the mixture was extracted with EtOAc (3×20 ml). The combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 7:3) provided 110 mg (0.30 mmol, 36%) N-[(3-Fluorophenyl)-methyl]-2-isopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid amide (example 23). [M+H]+372.2.

Source