N-methyl-2-pyrrolidone → HCID 21099439, compound

HRID 1351687Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].Br[C:13]1[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=1.[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[CH2:26])=[CH:23][CH:22]=1.CN1CCCC1=[O:35]>>[F:20][C:21]1[CH:28]=[CH:27][C:24](/[CH:25]=[CH:26]/[C:13]2[CH:18]=[CH:17][C:16]([S:19]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8]([NH2:11])(=[O:10])=[O:9])=[O:35])=[CH:15][CH:14]=2)=[CH:23][CH:22]=1

Participants

Reactant 4

HCID 13387N-methyl-2-pyrrolidone

HCID 660494-Bromothiophenol

HCID 678834-Fluorostyrene

HCID 1936632-Fluorobenzenesulfonamide

Product 1

HCID 21099439HCID 21099439, compound

Procedure

2-Fluorobenzenesulfonamide was reacted with 4-bromothiophenol according to the method of Example 46 Step 1 using 1-methyl-2-pyrrolidinone as solvent. The resulting thioether was oxidised to the corresponding sulfoxide by the procedure of Example 16 Step 1. This was coupled with 4-fluorostyrene by the procedure of Example 107 to give the title compound. δH (500 MHz, d6 DMSO): 8.10 (1H, d, J=7.8 Hz), 7.91 (1H, d, J=7.7 Hz), 7.87 (2H, s), 7.81 (1H, t, J=7.4 Hz), 7.71–7.63 (7 H, m), 7.31 (1H, d, J=16.5 Hz), 7.22–7.18 (3H, m).

Sources & evidence

ORD record: ord-341c0406da8142a4b1a1a2df2b285bd5
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217740B2

Reaction notes

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