1-Bromopropane → methyl 2-[N-(5-bromo-2-propoxybenzyl)-N-ethylamino]pyridine-5-carboxylate

HRID 1604370Notes

Reaction equation

HRID 1604370 reaction equation
Br[CH2:2][CH2:3][CH3:4].[Br:5][C:6]1[CH:7]=[CH:8][C:9]([OH:26])=[C:10]([CH:25]=1)[CH2:11][N:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][N:16]=1)[CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([O:26][CH2:2][CH2:3][CH3:4])=[C:10]([CH:25]=1)[CH2:11][N:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][N:16]=1)[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 11728230methyl 2-[N-(2-hydroxy-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylate

Product 1

HCID 22622503methyl 2-[N-(5-bromo-2-propoxybenzyl)-N-ethylamino]pyridine-5-carboxylateYield 54.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Bromopropane (0.12 g, 0.69 mmol) was treated with a solution of methyl 2-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-5-pyridylcarboxylate (0.2 g, 0.55 mmol) in DMF (4 ml). Potassium carbonate (230 mg, 1.7 mmol) was added to this solution and the reaction mixture was stirred for 18 hours. The solvent was evaporated and the residue taken up in water (4 ml) and extracted with ethyl acetate (3×3 ml). The combined extracts were evaporated and the residue subjected to chromatography (eluant: ethyl acetate/hexane) to give the title compound as a pale yellow oil (0.122 g, 54%) which was used in the subsequent step without further purification.

Workup

  1. customThe solvent was evaporated
  2. extractionextracted with ethyl acetate (3×3 ml)
  3. customThe combined extracts were evaporated

Sources & evidence

ORD record
ord-e11308629a88470ea96df9606330aa61
Source dataset
uspto-grants-1999_11
Patent number
US05994353

Reaction notes

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