Water → HCID 59265031, compound

HRID 646191Notes

Reaction equation

HRID 646191 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][O:7][C:8]2[C:9]([CH2:15][CH2:16][NH2:17])=[N:10][C:11]([CH3:14])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[CH:20]([C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1)=O.[BH4-].[Na+].O>C(O)C>[Br:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][O:7][C:8]2[C:9]([CH2:15][CH2:16][NH:17][CH2:20][C:22]3[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=3)=[N:10][C:11]([CH3:14])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 15294Methyl 4-FormylbenzoateHCID 4311764Sodium borohydrideHCID 59265032HCID 59265032, compound

Product 1

HCID 59265031HCID 59265031, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 675 mg (2.10 mmol) of 2-{3-[(4-bromobenzyl)oxy]-6-methyl-2-pyridinyl}ethylamine and 345 mg (2.10 mmol) of methyl 4-formylbenzoate in 5 ml of ethanol is heated at reflux for two hours. The solvent is then removed under reduced pressure and the resulting residue is dissolved in 5 ml of methanol. A total of 159 mg (4.21 mmol) of solid NaBH4 are added a little at a time. After two hours of stirring at room temperature, the mixture is poured into water and extracted with ethyl acetate. The organic extract is washed with saturated sodium chloride solution and dried over Na2SO4. After filtration, the solvent is removed under reduced pressure and the resulting crude product is purified by preparative HPLC. This gives 351 mg (0.75 mmol, 35% yield) of a colorless oil.

Workup

  1. temperatureat reflux for two hours
  2. customThe solvent is then removed under reduced pressure
  3. dissolutionthe resulting residue is dissolved in 5 ml of methanol
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. washis washed with saturated sodium chloride solution
  7. dry with materialdried over Na2SO4
  8. filtrationAfter filtration
  9. customthe solvent is removed under reduced pressure
  10. customthe resulting crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-1a8945d648e341109d09e68ba00679e6
Source dataset
uspto-grants-2010_04
Patent number
US07705043B2

Reaction notes

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