Sodium hydride → 1-[(1,2-Dimethyl-1H-imidazol-4-yl)sulfonyl]-4-methyl-5-phenyl-1H-pyrrole-3-carbaldehyde

HRID 2196922Notes

Reaction equation

HRID 2196922 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.[CH3:32][N:33]1[CH:37]=[C:36]([S:38](Cl)(=[O:40])=[O:39])[N:35]=[C:34]1[CH3:42]>>[CH3:32][N:33]1[CH:37]=[C:36]([S:38]([N:5]2[C:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[C:2]([CH3:1])[C:3]([CH:13]=[O:14])=[CH:4]2)(=[O:40])=[O:39])[N:35]=[C:34]1[CH3:42]

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 27362561,2-Dimethylimidazole-4-sulfonyl chlorideHCID 713628124-Methyl-5-phenyl-1H-pyrrole-3-carbaldehyde

Product 1

HCID 866207651-[(1,2-Dimethyl-1H-imidazol-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 (1,2-dimethyl-1H-imidazol-4-yl)sulfonyl chloride (253 mg), the title compound was obtained as a colorless solid (yield 294 mg, 86%).

Workup

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

Sources & evidence

ORD record
ord-ee56fd1149f6404984b4f6665d112c20
Source dataset
uspto-grants-2012_12
Patent number
US08338461B2

Reaction notes

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