Sodium → (5-Fluoro-2-phenoxy-phenyl)-{5-methoxy-2-[2-(mesyloxy-)-ethoxy]-benzyl}-amine

HRID 1717514Notes

Reaction equation

HRID 1717514 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([NH2:8])[CH:7]=1.[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([O:26][CH2:27][CH2:28][O:29][S:30]([CH3:33])(=[O:32])=[O:31])=[C:22]([CH:25]=1)[CH:23]=O.[Na]>ClC(Cl)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([NH:8][CH2:23][C:22]2[CH:25]=[C:18]([O:17][CH3:16])[CH:19]=[CH:20][C:21]=2[O:26][CH2:27][CH2:28][O:29][S:30]([CH3:33])(=[O:31])=[O:32])[CH:7]=1

Participants

6

Reactant 3

HCID 5360545SodiumHCID 196271325-Fluoro-2-phenoxyanilineHCID 597658555-Methoxy-2-(2-mesyloxyethoxy)-benzaldehyde

Product 1

HCID 86621787(5-Fluoro-2-phenoxy-phenyl)-{5-methoxy-2-[2-(mesyloxy-)-ethoxy]-benzyl}-amineYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To stirred solution of 9.1 g (45 mmol) 1b, 12.3 g (45 mmol) 4a and one drop of glacial acid in 60 ml dichloroethane (pH=5) were added 14.8 g (70 mmol) sodium tris-acetoxy hydro borane. The reaction mixture was stirred over night and diluted with 5 ml water. The pH value was adjusted with aqueous sodium hydroxyd solution to pH=8-9. The mixture was extracted three times with dichloromethane. The combined organic phases were washed with water and brine and were dried with magnesium sulfate. The desired crude product 4b was obtained in 62% yield (12.9 g, 27.9 mmol) as yellow oil. The crude product 4b was used without further purification.

Workup

  1. extractionThe mixture was extracted three times with dichloromethane
  2. washThe combined organic phases were washed with water and brine
  3. dry with materialwere dried with magnesium sulfate

Sources & evidence

ORD record
ord-787d6f34270a46d5a6eeb4857bbad118
Source dataset
uspto-grants-2010_09
Patent number
US07803960B2

Reaction notes

Loading…