Tert-butyl 2-cyano-5-{4-{(ethylsulfonyl)amino]phenyl}-1H-pyrrole-1-carboxylate → N-[4-(5-Cyano-1H-pyrrol-2-yl)phenyl]ethanesulfonamide

HRID 1591838Notes

Reaction equation

C(OC([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])=[CH:15][CH:14]=2)=[CH:11][CH:10]=[C:9]1[C:25]#[N:26])=O)(C)(C)C>CC(N(C)C)=O>[C:25]([C:9]1[NH:8][C:12]([C:13]2[CH:14]=[CH:15][C:16]([NH:19][S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])=[CH:17][CH:18]=2)=[CH:11][CH:10]=1)#[N:26]

Participants

Conditions

Temperature: 170 °C

Procedure

Tert-butyl-2-cyano-5-{4-{(ethylsulfonyl)amino]phenyl}-1H-pyrrole-1-carboxylate (2.3 g, 6.1 mmol) was dissolved in dimethylacetamide (60 mL) and heated to 170° C. for 30 minutes. The mixture was cooled and partitioned between water and ethyl acetate. The organic layers were dried over magnesium sulfate, and concentrated. The residue was purified by silica gel Flash Chromatography (hexane/ethyl acetate; 1:1) to afford the title compound (1.51 g, 90%).

Workup

temperatureThe mixture was cooled
custompartitioned between water and ethyl acetate
dry with materialThe organic layers were dried over magnesium sulfate
concentrationconcentrated
customThe residue was purified by silica gel Flash Chromatography (hexane/ethyl acetate; 1:1)

Sources & evidence

ORD record: ord-a4fb00caf82848528b29c9969102c477
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291643B2

Reaction notes

Loading…