Sodium hydride → Ethyl 4,5-dibromo-1-(4-fluorobenzyl)-2-({(2-ethoxy-2-oxoethyl)[(4-methylphenyl)sulfonyl]amino}methyl)-1H-pyrrole-3-carboxylate

HRID 640701Notes

Reaction equation

HRID 640701 reaction equation
[Br:1][C:2]1[C:3]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:4]([CH2:16]Br)[N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:6]=1[Br:7].[CH3:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])(=[O:32])=[O:31])=[CH:26][CH:25]=1.[H-].[Na+]>C1COCC1>[Br:1][C:2]1[C:3]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:4]([CH2:16][N:33]([CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[S:30]([C:27]2[CH:26]=[CH:25][C:24]([CH3:23])=[CH:29][CH:28]=2)(=[O:32])=[O:31])[N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:6]=1[Br:7]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 230685Ethyl 2-(4-methylphenylsulfonamido)acetateHCID 53237464ethyl 4,5-dibromo-2-(bromomethyl)-1-(4-fluorobenzyl)-1H-pyrrole-3-carboxylate

Product 1

HCID 59855815Ethyl 4,5-dibromo-1-(4-fluorobenzyl)-2-({(2-ethoxy-2-oxoethyl)[(4-methylphenyl)sulfonyl]amino}methyl)-1H-pyrrole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of ethyl 4,5-dibromo-2-(bromomethyl)-1-(4-fluorobenzyl)-1H-pyrrole-3-carboxylate (104.0 g, 0.209 mol) and ethyl N-[(4-methylphenyl)sulfonyl]glycinate (53.7 g, 0.209 mol, prepared by the method of: Ginzel, K. D.; Brungs, P.; Steckhan, E. Tetrahedron 1989, 45, 1691-1701) in anhydrous THF (1.5 L) was added NaH (60% in mineral oil, 8.409, 0.210 mol) in several small portions. The mixture was allowed to stir at room temperature for 16 hours. It was quenched with aq. NH4Cl solution, and extracted with ethyl acetate. The organic layer was dried over Na2SO4, concentrated and the residue was purified by column chromatography with ethyl acetate/hexane (1:4, v:v) to provide the title compound as glue-like material (124 g, 88% yield).

Workup

  1. customIt was quenched with aq. NH4Cl solution
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography with ethyl acetate/hexane (1:4, v:v)

Sources & evidence

ORD record
ord-3ac599957adc419292c6ed1482ab95d9
Source dataset
uspto-grants-2010_04
Patent number
US07692014B2

Reaction notes

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