Dimethylformamide → 3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole-2-carbonitrile

HRID 1189552Notes

Reaction equation

[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([CH3:22])[C:6]=1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)(=[O:16])=[O:15].[CH3:23][N:24](C=O)C>C(#N)C>[CH3:22][C:5]1[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[S:14]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)(=[O:16])=[O:15])=[C:2]([CH3:1])[NH:3][C:4]=1[C:23]#[N:24]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 2,4-dimethyl-3-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole (128.0 mg, 0.402 mmol) and N-chlorosulfonylisocyanide (43.7 μl, 0.502 mmol) in acetonitrile (2.0 ml) was stirred at 25° C. for 1 hour. DMF (31.1 μl, 0.402 mmol) was then added and the resulting mixture was stirred for an additional 16 h at room temperature. The reaction was quenched with water (100 ml) and extracted with dichloromethane (100 ml×2). The organic layers were combined, filtered, and evaporated to give an oil. The oil was purified by column chromatography (0 to 50% ethyl acetate in hexanes) to give 3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole-2-carbonitrile (49.6 mg, 0.144 mmol, 35.9% yield).

Workup

stirringthe resulting mixture was stirred for an additional 16 h at room temperature
customThe reaction was quenched with water (100 ml)
extractionextracted with dichloromethane (100 ml×2)
filtrationfiltered
customevaporated
customto give an oil
customThe oil was purified by column chromatography (0 to 50% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-28207d1f1a394b56b2cae279f627016e
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674115B2

Reaction notes

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