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

HRID 427751
Notes
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Reaction equation

HRID 427751 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>[CH2:16]([O:23][C:24]1[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][C:25]=1[CH2:26][N:3]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=1)[CH2:1][CH3:2])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228Dimethylformamide
Solvent
2×

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-cc5d7011b8f9433baf330acb4d2f45dc
Source dataset
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06313148B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes