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

HRID 1455969Notes

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]

Participants

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

temperatureto warm to ambient temperature
stirringstirred for 18 hours
washThe combined organic extracts were washed once with brine
dry with materialdried (MgSO4)
customevaporated
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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