Phosphorus oxychloride → Methyl 2-chloro-6-(2-fluoro-5-methoxyphenyl)-5-isobutoxynicotinate

HRID 709769Notes

Reaction equation

HRID 709769 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:15]([O:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:14][C:13]([C:21]([O:23][CH3:24])=[O:22])=[CH:12][N+:11]=1[O-].P(Cl)(Cl)([Cl:28])=O>>[Cl:28][C:12]1[N:11]=[C:10]([C:3]2[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=2[F:1])[C:15]([O:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:14][C:13]=1[C:21]([O:23][CH3:24])=[O:22]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1177600222-(2-Fluoro-5-methoxyphenyl)-3-isobutoxy-5-(methoxycarbonyl)pyridine 1-oxide

Product 1

HCID 117760273Methyl 2-chloro-6-(2-fluoro-5-methoxyphenyl)-5-isobutoxynicotinate

Procedure

A mixture of 2-(2-fluoro-5-methoxyphenyl)-3-isobutoxy-5-(methoxycarbonyl)pyridine 1-oxide (600 mg) and phosphoryl chloride (5.0 mL) was heated under reflux for 1 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (315 mg) as a pale-yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-fcd921f0e81e4997a1dcb738430eb827
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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