Stannane, tributyl(1-methylethenyl)- → HCID 53628636, compound

HRID 1260216Notes

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-dad33c5c6478474d9c0cb822931c35b5
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470810B2

Reaction notes

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