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

HRID 1771813Notes

Reaction equation

HRID 1771813 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH2:16][NH:17][C:18]3[C:19]([CH3:26])=[C:20]([OH:25])[CH:21]=[CH:22][C:23]=3[CH3:24])[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:34][C:35]([O:37][CH:38]([CH3:40])[CH3:39])=[O:36].O>CC(=O)CC>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH2:16][NH:17][C:18]3[C:19]([CH3:26])=[C:20]([CH:21]=[CH:22][C:23]=3[CH3:24])[O:25][CH2:34][C:35]([O:37][CH:38]([CH3:40])[CH3:39])=[O:36])[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 121593Isopropyl bromoacetateHCID 894438453-[[3-(3-Fluorophenyl)-5-methoxy-phenyl]methylamino]-2,4-dimethyl-phenol

Product 1

HCID 89443955Isopropyl 2-[3-[[3-(3-fluorophenyl)-5-methoxy-phenyl]methylamino]-2,4-dimethyl-phenoxy]acetateYield 63.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 3-[[3-(3-fluorophenyl)-5-methoxy-phenyl]methylamino]-2,4-dimethyl-phenol (700 mg, 2.0 mmol, 1.0 eq) in 2-butanone (4 mL) was added Cs2CO3 (973 mg, 3 mmol, 1.5 eq). The reaction mixture was stirred for 30 min then isopropyl bromoacetate (432 mg, 2.4 mmol, 1.2 eq) was added. The reaction mixture was stirred at room temperature for a further 1 h then poured into water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by column chromatography (petroleum ether:EtOAc, 100:0 to 30:1) to give the title compound as a colorless oil (570 mg, 63%).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for a further 1 h
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography (petroleum ether:EtOAc, 100:0 to 30:1)

Sources & evidence

ORD record
ord-414f76f9f4fa4761907d343270a4a30c
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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