Sodium hydride → 1-[(5-Chloro-1,3-dimethyl-1H-pyrazol-4-yl)sulfonyl]-4-methyl-5-phenyl-1H-pyrrole-3-carbaldehyde

HRID 1782249Notes

Reaction equation

HRID 1782249 reaction equation
[CH3:1][C:2]1[C:3]([CH:13]=[O:14])=[CH:4][NH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.[Cl:32][C:33]1[N:37]([CH3:38])[N:36]=[C:35]([CH3:39])[C:34]=1[S:40](Cl)(=[O:42])=[O:41]>>[Cl:32][C:33]1[N:37]([CH3:38])[N:36]=[C:35]([CH3:39])[C:34]=1[S:40]([N:5]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:2]([CH3:1])[C:3]([CH:13]=[O:14])=[CH:4]1)(=[O:41])=[O:42]

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 27771265-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonyl chlorideHCID 713628124-Methyl-5-phenyl-1H-pyrrole-3-carbaldehyde

Product 1

HCID 866207661-[(5-Chloro-1,3-dimethyl-1H-pyrazol-4-yl)sulfonyl]-4-methyl-5-phenyl-1H-pyrrole-3-carbaldehyde

Procedure

By a reaction under similar conditions as in Reference Example 65 and using 4-methyl-5-phenyl-1H-pyrrole-3-carbaldehyde (185 mg), sodium hydride (60% in oil, 60 mg), 15-crown-5 (0.30 mL) and (5-chloro-1,3-dimethyl-1H-pyrazol-4-yl)sulfonyl chloride (298 mg), the title compound was obtained as an oil (yield 379 mg, about 100%).

Workup

  1. customBy a reaction under similar conditions as in Reference Example 65

Sources & evidence

ORD record
ord-eaf0169436754701ae6ff1e949eba783
Source dataset
uspto-grants-2009_03
Patent number
US07498337B2

Reaction notes

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