Sodium hydride → methyl 2-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylate

HRID 840300Notes

Reaction equation

HRID 840300 reaction equation
[CH2:1]([NH:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=1)[CH3:2].[H-].[Na+].[CH2:16]([O:23][C:24]1[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][C:25]=1[CH2:26]Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH3:11][O:10][C:8]([C:7]1[CH:12]=[CH:13][C:4]([N:3]([CH2:26][C:25]2[CH:28]=[C:29]([Br:32])[CH:30]=[CH:31][C:24]=2[O:23][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:1][CH3:2])=[N:5][CH:6]=1)=[O:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11126856Methyl 6-(ethylamino)pyridine-3-carboxylateHCID 117832201-(Benzyloxy)-4-bromo-2-(bromomethyl)benzene

Product 1

HCID 22622546methyl 2-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylateYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of methyl 6-ethylaminonicotinoate (15.2 g, 84.4 mmol) in DMF (50 ml) was cooled to 0 ° C. and treated with sodium hydride (60%, 75 mmol). The reaction was stirred for 1 hour and a solution of 2-benzyloxy-5-bromobenzylbromide (25 g, 70.2 mmol) in DMF (50 ml) added. The reaction was allowed to warm to ambient temperature and stirred for 18 hours. The reaction was quenched with water and extracted with ethyl acetate (three times). The organic layers were combined, washed with water and brine twice, dried (MgSO4) and evaporated to give a white solid. Recrystallisation from ethyl acetate/hexane gave methyl-2-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylate (22.7 g, 71%).

Workup

  1. stirringstirred for 18 hours
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate (three times)
  4. washwashed with water and brine twice
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give a white solid
  8. customRecrystallisation from ethyl acetate/hexane

Sources & evidence

ORD record
ord-f0fda7f9849b47e8a01071e6e8bca003
Source dataset
uspto-grants-2002_04
Patent number
US06365603B1

Reaction notes

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