4-Toluenesulfonyl chloride → HCID 66924908, compound

HRID 554188Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[NH:8][CH:7]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:5]=1[CH3:14].[S:15](Cl)([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)(=[O:17])=[O:16]>>[Br:3][C:4]1[N:8]([S:15]([C:18]2[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:7]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:5]=1[CH3:14]

Participants

Reactant 3

HCID 73974-Toluenesulfonyl chloride

HCID 24758Sodium hydride

HCID 66925114Ethyl 5-bromo-4-methyl-1H-pyrrole-3-carboxylate

Product 1

HCID 66924908HCID 66924908, compoundYield 86%

Procedure

Using sodium hydride (60% in oil, 620 mg), ethyl 5-bromo-4-methyl-1H-pyrrole-3-carboxylate (3.0 g) and tosyl chloride (2.95 g), a procedure as in Reference Example 41 was performed to give the title compound as pale-yellow crystals (yield 4.27 g, 86%).

Sources & evidence

ORD record: ord-bcb1c1e05eaf4cb8bafa0176716938a2
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048909B2

Reaction notes

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