Stannane, tributyl(1-methylethenyl)- → 2-Fluoro-4-isopropenyl-N-[4-((S)-1-propyl-pyrrolidin-3-yl)-phenyl]-benzenesulfonamide

HRID 2262601Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6](Br)[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C@@H:19]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH3:26])[CH2:20]2)=[CH:15][CH:14]=1)(=[O:11])=[O:10].[CH2:27]([Sn](CCCC)(CCCC)C(C)=C)[CH2:28][CH2:29]C>O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([C:28]([CH3:29])=[CH2:27])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C@@H:19]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH3:26])[CH2:20]2)=[CH:15][CH:14]=1)(=[O:11])=[O:10]

Participants

Conditions

Temperature: 150 °C

Procedure

0.2 g of 2-fluoro-4-bromo-N-[4-((S)-1-propyl-pyrrolidin-3-yl)-phenyl]-benzenesulfonamide (0.45 mmol), 1.05 g of tributyl-isopropenyl-stannane (3.17 mmol) and 0.026 g of tetrakistriphenylphosphinpalladium(0) (0.02 mmol) were dissolved in 3 ml of tetrahydrofuran and stirred for 40 minutes at 150° C. in the microwave (CEM). The reaction mixture was filtered over celite, washed with methanol, and the filtrate evaporated to dryness under reduced pressure. The residue was purified via silica gel chromatography with cyclohexane/ethyl acetate (20%), ethyl acetate, and ethyl acetate/methanol (15%). Fractions containing the product were combined, the solvent evaporated to yield 0.176 g of the title product.

Workup

filtrationThe reaction mixture was filtered over celite
washwashed with methanol
customthe filtrate evaporated to dryness under reduced pressure
customThe residue was purified via silica gel chromatography with cyclohexane/ethyl acetate (20%), ethyl acetate, and ethyl acetate/methanol (15%)
additionFractions containing the product
customthe solvent evaporated

Sources & evidence

ORD record: ord-2d9ce1d8e5b64438bafc8bc0841b9227
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851463B2

Reaction notes

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