Water → HCID 86761999, compound

HRID 1890446Notes

Reaction equation

HRID 1890446 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][N:5]=1)(=O)[CH3:2].[BH4-].[Na+].[OH2:13]>CO>[OH:13][CH2:2][CH:1]=[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][NH:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 231453451-(5-Bromopyridin-2-yl)ethan-1-one

Product 1

HCID 86761999HCID 86761999, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-acetyl-5-bromopyridine (1 g, 5.0 mmol) (Bioorg. Med. Chem., 13, 2005, 6763-6770.) is dissolved in methanol (10 mL), and stir at room temperature. NaBH4 (0.57 g, 15 mmol) is added in batches and stir at room temperature for 10 minutes. TLC (petroleum ether/ethyl acetate=10:1) is used to monitor the reaction. Once the reaction is completed, add water (15 mL) into the reaction solution, and stir for 0.5 hours. After that, methanol is evaporated, extract with dichloromethane (25 mL×3), merge the organic phases, followed by anhydrous Na2SO4 drying and filtering. The solvent is evaporated to obtain 0.93 g of oily liquid (Compound 42-A). The yield is 91.9%.

Workup

  1. stirringstir at room temperature for 10 minutes
  2. customthe reaction
  3. stirringstir for 0.5 hours
  4. customAfter that, methanol is evaporated
  5. extractionextract with dichloromethane (25 mL×3)
  6. filtrationfiltering
  7. customThe solvent is evaporated

Sources & evidence

ORD record
ord-eff227e28667484b82ca5a7f2be5e7d1
Source dataset
uspto-grants-2013_08
Patent number
US08507481B2

Reaction notes

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