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 889508Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 40 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-e706388a277443a7ac4d5c5019a90da5
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252842B2

Reaction notes

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