Isopropanol → Isopropyl 2-[3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate

HRID 1771773Notes

Reaction equation

HRID 1771773 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:4][C:3]=1[CH2:15][NH:16][C:17]1[C:18]([CH3:29])=[C:19]([CH:25]=[CH:26][C:27]=1[CH3:28])[O:20][CH2:21][C:22]([OH:24])=[O:23].O=S(Cl)Cl.[CH3:34][CH:35](O)[CH3:36]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:4][C:3]=1[CH2:15][NH:16][C:17]1[C:18]([CH3:29])=[C:19]([CH:25]=[CH:26][C:27]=1[CH3:28])[O:20][CH2:21][C:22]([O:24][CH:35]([CH3:36])[CH3:34])=[O:23]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 24386Thionyl ChlorideHCID 894438132-[3-[[2Fluoro-5-(3-fluorophenyl)phenyl]methylamino]-2,4-dimethyl-phenoxy]acetic acid

Product 1

HCID 89467104Isopropyl 2-[3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-2,4-dimethyl-phenoxy]acetateYield 90%

Procedure

A solution of 2-[3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-2,4-dimethyl-phenoxy]acetic acid (I(j)) (120 mg, 0.3 mmol, 1 eq) and SOCl2 (1 mL) in i-PrOH (4 mL) was heated at reflux for 2 h. The solvent was evaporated in vacuo and the residue was taken up in water and basified to pH 8 by addition of aqueous NaHCO3. The mixture was extracted with EtOAc and the organic extract was dried (Na2SO4) filtered and evaporated in vacuo. The residue obtained was purified by column chromatography to give the title compound as an oil (120 mg, 90%).

Workup

  1. temperatureat reflux for 2 h
  2. customThe solvent was evaporated in vacuo
  3. additionthe residue was taken up in water and basified to pH 8 by addition of aqueous NaHCO3
  4. extractionThe mixture was extracted with EtOAc
  5. extractionthe organic extract
  6. dry with materialwas dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue obtained
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-222db2b99ec747adb41bfc6693011aa2
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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