1-(Prop-2-en-1-yl)cyclopropane-1-sulfonyl chloride → 1-Allyl-N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-6-methoxyphenyl)cyclopropane-1-sulfonamide

HRID 240986Notizen

Reaktionsgleichung

[F:1][C:2]1[C:7]([F:8])=[C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=2[F:17])[C:5]([NH2:18])=[C:4]([O:19][CH3:20])[CH:3]=1.[CH2:21]([C:24]1([S:27](Cl)(=[O:29])=[O:28])[CH2:26][CH2:25]1)[CH:22]=[CH2:23]>N1C=CC=CC=1>[CH2:21]([C:24]1([S:27]([NH:18][C:5]2[C:4]([O:19][CH3:20])=[CH:3][C:2]([F:1])=[C:7]([F:8])[C:6]=2[NH:9][C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=2[F:17])(=[O:29])=[O:28])[CH2:26][CH2:25]1)[CH:22]=[CH2:23]

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

To a stirred solution of 5,6-difluoro-N1-(2-fluoro-4-iodophenyl)-3-methoxybenzene-1,2-diamine (1 eq) in anhydrous pyridine (5 ml/mmole) was added 1-allyl-cyclopropanesulfonyl chloride (1-5 eq). The reaction mixture was stirred at 40° C. for 48 hours. The reaction mixture was partitioned with water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica to obtain the title product. 1H NMR (CDCl3, 300 MHz): δ 7.417 (dd, 1H), 7.309 (s, 1H), 7.25 (m, 1H), 6.89 (m, 1H), 6.52 (m, 1H), 6.427 (m, 1H), 6.03 (s, 1H), 5.668 (m, 1H), 5.11 (t, 1H), 3.9 (s, 3H), 2.75 (d, 2H), 1.21 (m, 2H), 0.767 (m, 2H).

Aufarbeitung

customThe reaction mixture was partitioned with water and ethyl acetate
washThe organic layer was washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated under reduced pressure
customThe residue was purified by flash column chromatography on silica

Quellen und Nachweise

ORD-Eintrag: ord-af8c8e90e53f41d2ad689b39591bee8b
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08648116B2

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