Methanol → HCID 59506274, compound

HRID 1098743Notes

Reaction equation

HRID 1098743 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17](=O)[CH3:18])=[CH:13][C:12]=2[Br:20])[CH:7]=[N:6][CH:5]=1.CO.C([BH3-])#[N:25].[Na+]>>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([NH2:25])[CH3:18])=[CH:13][C:12]=2[Br:20])[CH:7]=[N:6][CH:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 59506149Methyl-5-(4-acetyl-2-bromo-phenoxy)-nicotinate

Product 1

HCID 59506274HCID 59506274, compoundYield 96.4%

Procedure

To a solution of the compound from step 1 (630 mg, 1.79 mmol) in MeOH (30 mL) ammonium acetate (1.39 g, 17.9 mmol) was added. After stirring at ambient temperature overnight sodium cyanoborohydride (135.7 mg, 2.16 mmol) was added and the reaction was refluxed for 6 h. The solvent was evaporated and the solid, dissolved in ethyl acetate, was extracted with water. The organic layer was separated, washed with brine, dried over sodium sulphate, filtered and evaporated to give 606 mg (yield: 96%) of the crude product. LC/MS (method D) (M+H)+: 352

Workup

  1. additionwas added
  2. temperaturethe reaction was refluxed for 6 h
  3. customThe solvent was evaporated
  4. dissolutionthe solid, dissolved in ethyl acetate
  5. extractionwas extracted with water
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over sodium sulphate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-867365f4300e45ffad1f839adf55f0f9
Source dataset
uspto-grants-2012_03
Patent number
US08143242B2

Reaction notes

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