Hydrochloric Acid → 3,5-Dichloro-2-fluoro-4-(3-isopropyl-4-methoxyphenoxy)-6-methoxycarbonylmethoxypyridine

HRID 352550Notes

Reaction equation

HRID 352550 reaction equation
[Cl:1][C:2]1[C:3](F)=[N:4][C:5]([F:21])=[C:6]([Cl:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1.[C:23]([O:27][CH3:28])(=[O:26])[CH2:24][OH:25].[H-].[Na+].Cl>C1COCC1.[Cl-].[Na+].O>[Cl:20][C:6]1[C:5]([F:21])=[N:4][C:3]([O:25][CH2:24][C:23]([O:27][CH3:28])=[O:26])=[C:2]([Cl:1])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 66774Methyl GlycolateHCID 227120853,5-Dichloro-2,6-difluoro-4-(3-isopropyl-4-methoxyphenoxy)pyridine

Product 1

HCID 227120693,5-Dichloro-2-fluoro-4-(3-isopropyl-4-methoxyphenoxy)-6-methoxycarbonylmethoxypyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3,5-dichloro-2,6-difluoro-4-(3-isopropyl-4-methoxyphenoxy)pyridine (100 mg) and methyl glycolate (neat, 25 μl) in THF (2.0 mL) was added a 60% oil dispersion of sodium hydride (10 mg) in one portion. The resulting mixture was stirred at ambient temperature for 30 min. The reaction mixture was diluted with brine, neutralized with 1 N HCl, extracted with CH2Cl2 (50 mL×2), dried (Na2SO4) and concentrated in vacuo to afford the title compound as a colorless oil (120 mg).

Workup

  1. extractionextracted with CH2Cl2 (50 mL×2)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6a485c966ffd4fa38832616f5fdbdedd
Source dataset
uspto-grants-2004_06
Patent number
US06747048B2

Reaction notes

Loading…