Potassium Carbonate → methyl 2-[N-(5-bromo-2-(4-pyridylmethoxy)benzyl)-N-ethylamino]pyridine-5-carboxylate

HRID 1455975Notes

Reaction equation

HRID 1455975 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[Br:16][C:17]1[CH:18]=[CH:19][C:20]([OH:37])=[C:21]([CH:36]=1)[CH2:22][N:23]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([O:34][CH3:35])=[O:33])=[CH:28][N:27]=1)[CH2:24][CH3:25]>CN(C=O)C.O>[Br:16][C:17]1[CH:18]=[CH:19][C:20]([O:37][CH2:3][C:4]2[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=2)=[C:21]([CH:36]=1)[CH2:22][N:23]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([O:34][CH3:35])=[O:33])=[CH:28][N:27]=1)[CH2:24][CH3:25]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 11728230methyl 2-[N-(2-hydroxy-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylate

Product 1

HCID 22105607methyl 2-[N-(5-bromo-2-(4-pyridylmethoxy)benzyl)-N-ethylamino]pyridine-5-carboxylateYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4-chloromethylpyridine hydrochloride (0.12 g, 0.73 mmol) in DMF (3 ml) was treated with potassium carbonate (0.29 g, 2.10 mmol). A solution of methyl 2-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]pyridine-5-carboxylate (0.26 g, 0.71 mmol) in DMF (4 ml) was added. The reaction was stirred for 24 hours and then the reaction was diluted with water and extracted with ethyl acetate (×3). The organic phases were combined and washed with water and brine once, dried (MgSO4) and evaporated. Chromatography eluant: ethyl acetate/hexane gave methyl 2-[N-(5-bromo-2-(4-pyridylmethoxy)benzyl)-N-ethylamino]pyridine-5-carboxylate as a white solid (0.209 g, 65%).

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. washwashed with water and brine once
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-c583b60c2edc4b0891c0e3bf096f7707
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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