Sodium hydride → Methyl 5-bromo-1-{[3-(methylsulfonyl)phenyl]sulfonyl}-1H-pyrrole-3-carboxylate

HRID 554262Notes

Reaction equation

[Br:1][C:2]1[NH:6][CH:5]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[CH:3]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.[CH3:28][S:29]([C:32]1[CH:33]=[C:34]([S:38](Cl)(=[O:40])=[O:39])[CH:35]=[CH:36][CH:37]=1)(=[O:31])=[O:30]>>[Br:1][C:2]1[N:6]([S:38]([C:34]2[CH:35]=[CH:36][CH:37]=[C:32]([S:29]([CH3:28])(=[O:31])=[O:30])[CH:33]=2)(=[O:40])=[O:39])[CH:5]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[CH:3]=1

Participants

Reactant 4

HCID 24758Sodium hydride

HCID 3633615-Crown-5

HCID 2203303-(Methylsulfonyl)benzenesulfonyl chloride

HCID 23271158Methyl 5-bromo-1H-pyrrole-3-carboxylate

Product 1

HCID 66924677Methyl 5-bromo-1-{[3-(methylsulfonyl)phenyl]sulfonyl}-1H-pyrrole-3-carboxylateYield 92%

Procedure

Using methyl 5-bromo-1H-pyrrole-3-carboxylate (2.89 g), sodium hydride (60% in oil, 850 mg), 15-crown-5 (4.69 g) and 3-methylsulfonylbenzenesulfonyl chloride (4.38 g), a procedure as in Reference Example 146 was performed to give the title compound as white crystals (yield 5.50 g, 92%).

Sources & evidence

ORD record: ord-1cd851f7461647e5ba82984777d70cd6
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048909B2

Reaction notes

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