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

HRID 427751
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 427751
[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
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Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cc5d7011b8f9433baf330acb4d2f45dc
Quelldatensatz
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06313148B1

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