Sodium hydride → 6-[(2-Benzylsulfanylbenzyl)ethylamino]nicotinic Acid Methyl Ester

HRID 545977Notes

Reaction equation

HRID 545977 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH3:12])=[N:6][CH:5]=1.[H-].[Na+].BrCC1C=CC=CC=1[CH:24]([SH:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[S:31][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11126856Methyl 6-(ethylamino)pyridine-3-carboxylateHCID 865877032-(2-Bromomethylphenyl sulfanylmethyl)benzene

Product 1

HCID 672068256-[(2-Benzylsulfanylbenzyl)ethylamino]nicotinic Acid Methyl EsterYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of methyl-6-ethylaminonicotinate in (59 mg, 0.332 mmol) DMF (0.8 mL) was added to sodium hydride (12 mg, 0.293 mL) in DMF (0.8 mL) at 0° C. The reaction was stirred for 1 hour and a solution of 2-(2-bromomethylphenyl sulfanylmethyl) benzene 5 (81 mg, 0.276 mmol) in 80 μL of DMF was added. The reaction was allowed to warm to ambient temperature and stirred for 18 hours. The solution was quenched with water and extracted with EtOAc (7×). The organic layers were combined, washed with water and brine twice, dried over MgSO4 and evaporated to give a white solid that was recrystallized from EtOAc/hexane. The solid was purified with 5% EtOAc/hexane by chromatography to yield 350 mg (70%) of the named compound.

Workup

  1. stirringstirred for 18 hours
  2. customThe solution was quenched with water
  3. extractionextracted with EtOAc (7×)
  4. washwashed with water and brine twice
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customto give a white solid
  8. customthat was recrystallized from EtOAc/hexane
  9. customThe solid was purified with 5% EtOAc/hexane by chromatography

Sources & evidence

ORD record
ord-bad053bfd33b4a0a8817a8fc2c9850e4
Source dataset
uspto-grants-2011_05
Patent number
US07935825B2

Reaction notes

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