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

HRID 1455969
Notes
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Reaction equation

HRID 1455969 reaction equation
[H-].[Na+].[CH2:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][N:7]=1)[CH3:4].[Br:16][C:17]1[CH:18]=[CH:19][C:20]([O:25][CH2:26][C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)=[C:21]([CH:24]=1)[CH2:22]Br.[Cl-].[NH4+]>CN(C=O)C>[S:28]1[CH:29]=[CH:30][CH:31]=[C:27]1[CH2:26][O:25][C:20]1[CH:19]=[CH:18][C:17]([Br:16])=[CH:24][C:21]=1[CH2:22][N:5]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][N:7]=1)[CH2:3][CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11126856Methyl 6-(ethylamino)pyridine-3-carboxylateHCID 221055055-Bromo-2-(2-thienylmethoxy)benzyl bromide

Product 1

HCID 22105529methyl 2-[N-(2-(2-thienylmethoxy)-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylateYield 8.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-5 °C

Procedure

A suspension of sodium hydride (50% dispersion 0.8 mmol, 38 mg) in DMF (2 ml) (sieve dried) was cooled to -5° C. and treated with methyl 2-(ethylamino)pyridine-5-carboxylate (0.145 g, 0.8 mmol). The reaction was stirred at -5° C. for 30 minutes and then treated with 5-bromo-2-(2-thienylmethoxy)benzyl bromide (0.29 g, 0.8 mmol) in DMF (0.5 ml). The reaction was allowed to warm to ambient temperature and stirred for 18 hours. The reaction was poured into saturated aqueous ammonium chloride. The combined organic extracts were washed once with brine, dried (MgSO4) and evaporated. The residue was purified by chromatography (eluant: diethyl ether/hexane) to give methyl 2-[N-(2-(2-thienylmethoxy)-5-bromobenzyl)N-ethylamino]pyridine-5-carboxylate as a colourless oil (0.03 g, 8%).

Workup

  1. temperatureto warm to ambient temperature
  2. stirringstirred for 18 hours
  3. washThe combined organic extracts were washed once with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by chromatography (eluant: diethyl ether/hexane)

Sources & evidence

ORD record
ord-90b2519442f947878d9920ee3e4fb4f7
Source dataset
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05843942

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes