Sodium → HCID 54209632, compound

HRID 1987836Notes

Reaction equation

HRID 1987836 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=1.[CH3:13][O-:14].[Na+].[Na]>CO>[CH3:13][O:14][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 127522376-Bromomethyl-nicotinic acid methyl ester

Product 1

HCID 54209632HCID 54209632, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

5.1 g (0.022 mol) of methyl 6-(bromomethyl)nicotinate [described in J. Med. Chem.; (2002), 45(23), 5005-5022], dissolved in 60 mL of methanol are added at room temperature to a solution of sodium methoxide obtained by adding 1 g (0.044 atom/g) of sodium to 40 mL of methanol. The reaction medium is then heated under reflux for 2 hours. The reaction medium is concentrated under vacuum and the residue is taken up in an aqueous solution of potassium hydrogen sulfate and dichloromethane. The organic phase is separated by decantation, dried over sodium sulfate and evaporated to dryness. 3.4 g of a yellow solid are obtained.

Workup

  1. customobtained
  2. temperatureThe reaction medium is then heated
  3. temperatureunder reflux for 2 hours
  4. concentrationThe reaction medium is concentrated under vacuum
  5. customThe organic phase is separated by decantation
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-993d9354c2fd4b60a1958f14a49da56a
Source dataset
uspto-grants-2009_06
Patent number
US07553845B2

Reaction notes

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