Sodium hydride → HCID 57522379, compound

HRID 554408Notes

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+].[S:24]1[CH:28]=[CH:27][C:26]([S:29]([Cl:32])(=[O:31])=[O:30])=[CH:25]1>>[ClH:32].[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:29]([C:26]2[CH:27]=[CH:28][S:24][CH:25]=2)(=[O:31])=[O:30])[CH:12]=1

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 2776378Thiophene-3-sulfonyl Chloride

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

Product 1

HCID 57522379HCID 57522379, compoundYield 35.4%

Procedure

Using tert-butyl methyl[(5-phenyl-1H-pyrrol-3-yl)methyl]carbamate (250 mg), sodium hydride (60% in oil, 140 mg) and thiophene-3-sulfonyl chloride (340 mg), a procedure as in Example 36 was performed to give the title compound as pale-purple crystals (yield 114 mg, 35%).

Sources & evidence

ORD record: ord-21dbe10ffb0b4e43bfe80e229d45f1c6
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048909B2

Reaction notes

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