Pyridine → N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-3-fluorophenyl]propane-2-sulfonamide

HRID 1591824Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[C:4]([F:16])[CH:3]=1.[CH:17]([S:20](Cl)(=[O:22])=[O:21])([CH3:19])[CH3:18].N1C=CC=CC=1>O>[C:14]([C:11]1[N:12]([CH3:13])[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:20]([CH:17]([CH3:19])[CH3:18])(=[O:22])=[O:21])=[CH:3][C:4]=2[F:16])=[CH:9][CH:10]=1)#[N:15]

Participants

Conditions

Temperature: 100 °C

Procedure

5-(4-amino-2-fluorophenyl)-1-methyl-1H-pyrrole-2-carbonitrile (200 mg, 0.93 mmol) was dissolved in isopropyl sulfonyl chloride (0.50 mL, 2.8 mmol), pyridine (0.2 mL) was added and the mixture was heated to 100° C. for 6 hours. The mixture was then cooled and diluted with water and extracted with ethyl acetate. The organics were combined, washed with water, brine, dried over MgSO4, and concentrated. Flash chromatography (0%-100% ethyl acetate in hexane) afforded N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-3-fluorophenyl]propane-2-sulfonamide (58 mg).

Workup

temperatureThe mixture was then cooled
extractionextracted with ethyl acetate
washwashed with water, brine
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-e17024f1d65a4795b31d6b1814552010
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291643B2

Reaction notes

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