Sodium hydride → 3-({4-[(Methylamino)methyl]-2-phenyl-1H-pyrrol-1-yl}sulfonyl)benzonitrile hydrochloride

HRID 554407Notes

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

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 28013603-Cyanobenzene-1-sulfonyl chloride

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

Product 1

HCID 669252433-({4-[(Methylamino)methyl]-2-phenyl-1H-pyrrol-1-yl}sulfonyl)benzonitrile hydrochlorideYield 58%

Procedure

Using tert-butyl methyl[(5-phenyl-1H-pyrrol-3-yl)methyl]carbamate (250 mg), sodium hydride (60% in oil, 175 mg) and 3-cyanobenzenesulfonyl chloride (528 mg), a procedure as in Example 36 was performed to give the title compound as pale-purple crystals (yield 195 mg, 58%).

Sources & evidence

ORD record: ord-b030c6d8e20a49aa80d89d8aa069bccc
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048909B2

Reaction notes

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