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

HRID 554237Notes

Reaction equation

[Br:1][C:2]1[NH:6][CH:5]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[C:3]=1[CH2:11][CH2:12][CH3:13].[H-].[Na+].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[Br:1][C:2]1[N:6]([S:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:24])=[O:23])[CH:5]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[C:3]=1[CH2:11][CH2:12][CH3:13]

Participants

Reactant 3

HCID 7369Benzenesulfonyl chloride

HCID 24758Sodium hydride

HCID 66924577Methyl 5-bromo-4-propyl-1H-pyrrole-3-carboxylate

Product 1

HCID 66924749Methyl 5-bromo-1-(phenylsulfonyl)-4-propyl-1H-pyrrole-3-carboxylateYield 85.2%

Procedure

Using methyl 5-bromo-4-propyl-1H-pyrrole-3-carboxylate (2.96 g), sodium hydride (60% in oil, 634 mg) and benzenesulfonyl chloride (2.33 g), a procedure as in Reference Example 41 was performed to give the title compound as colorless crystals (yield 3.96 g, 85%).

Sources & evidence

ORD record: ord-15e2a99d1fd547da8a47d19912c605de
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048909B2

Reaction notes

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