Benzenesulfonyl chloride → Methyl 5-bromo-4-ethyl-1-(phenylsulfonyl)-1H-pyrrole-3-carboxylate

HRID 554260Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[NH:8][CH:7]=[C:6]([C:9]([O:11][CH3:12])=[O:10])[C:5]=1[CH2:13][CH3:14].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[Br:3][C:4]1[N:8]([S:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:23])=[O:22])[CH:7]=[C:6]([C:9]([O:11][CH3:12])=[O:10])[C:5]=1[CH2:13][CH3:14]

Participants

Reactant 3

HCID 7369Benzenesulfonyl chloride

HCID 24758Sodium hydride

HCID 66924658Methyl 5-bromo-4-ethyl-1H-pyrrole-3-carboxylate

Product 1

HCID 66924922Methyl 5-bromo-4-ethyl-1-(phenylsulfonyl)-1H-pyrrole-3-carboxylateYield 91%

Procedure

Using sodium hydride (60% in oil, 393 mg), methyl 5-bromo-4-ethyl-1H-pyrrole-3-carboxylate (2.00 g) and benzenesulfonyl chloride (1.25 mL), a procedure as in Reference Example 41 was performed to give the title compound as white crystals (yield 2.93 g, 91%).

Sources & evidence

ORD record: ord-659c2ec58333417cb9eaac496877ae60
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048909B2

Reaction notes

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