Sodium hydride → 1-{1-[(4-Isopropoxyphenyl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}-N-methylmethanamine

HRID 554405

Reaction equation

C[N:2]([CH2:10][C:11]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:13][CH:12]=1)[C:3](=O)OC(C)(C)C.[H-].[Na+].[CH:24]([O:27][C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1)([CH3:26])[CH3:25]>>[CH:24]([O:27][C:28]1[CH:33]=[CH:32][C:31]([S:34]([N:13]2[C:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:15][C:11]([CH2:10][NH:2][CH3:3])=[CH:12]2)(=[O:36])=[O:35])=[CH:30][CH:29]=1)([CH3:26])[CH3:25]

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 223272974-(Propan-2-yloxy)benzene-1-sulfonyl chloride

HCID 57522146Tert-butyl methyl[(5-phenyl-1H-pyrrol-3-YL)methyl]carbamate

Product 1

HCID 669252911-{1-[(4-Isopropoxyphenyl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}-N-methylmethanamineYield 50%

Procedure

Using tert-butyl methyl[(5-phenyl-1H-pyrrol-3-yl)methyl]carbamate (70 mg), sodium hydride (60% in oil, 98 mg) and 4-isopropoxybenzenesulfonyl chloride (201 mg), a procedure as in Example 38 was performed to give the title compound as pale-red crystals (yield 47 mg, 45%).

Sources & evidence

ORD record: ord-fb4e21ab59614f68bf193d2a51f61da5
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048909B2

Linked notes

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