Chlorosulfonyl isocyanate → Tert-butyl 2-cyano-5-{4-{(ethylsulfonyl)amino]phenyl}-1H-pyrrole-1-carboxylate

HRID 1591837Notes

Reaction equation

[CH2:1]([S:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:15]=[CH:16][CH:17]=2)=[CH:9][CH:8]=1)(=[O:5])=[O:4])[CH3:2].ClS([N:29]=[C:30]=O)(=O)=O>O1CCCC1>[C:30]([C:15]1[N:14]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[C:13]([C:10]2[CH:9]=[CH:8][C:7]([NH:6][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[CH:12][CH:11]=2)=[CH:17][CH:16]=1)#[N:29]

Participants

Conditions

Temperature: -78 °C

Procedure

tert-Butyl 2-{4-[(ethylsulfonyl)amino]phenyl}-1H-pyrrole-1-carboxylate (3.0 g, 8.58 mmol) was dissolved in tetrahydrofuran (85 mL) and cooled to −78° C., followed by the slow addition of chlorosulfonyl isocyanate. After tert-Butyl 2-{4-[(ethylsulfonyl)amino]phenyl}-1H-pyrrole-1-carboxylate was consumed, dimethyl formamide (6.86 mL) was added and the solution allowed to warm to room temperature. After 2 hours, the mixture was cooled and partitioned between water and diethyl ether. The combined organic layers were dried over magnesium sulfate, and concentrated. The residue was purified by silica gel flash chromatography (hexane/ethyl acetate; 7:3) to afford the title compound (1.84 g, 57%). The title compound was used immediately in the next step.

Workup

customAfter tert-Butyl 2-{4-[(ethylsulfonyl)amino]phenyl}-1H-pyrrole-1-carboxylate was consumed
additiondimethyl formamide (6.86 mL) was added
temperatureto warm to room temperature
temperaturethe mixture was cooled
custompartitioned between water and diethyl ether
dry with materialThe combined organic layers were dried over magnesium sulfate
concentrationconcentrated
customThe residue was purified by silica gel flash chromatography (hexane/ethyl acetate; 7:3)

Sources & evidence

ORD record: ord-7fee40175bcb41cb9cc38f0cffe36a89
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291643B2

Reaction notes

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