Tributylvinyltin → 6-Methoxy-1-(phenylsulfonyl)-4-vinyl-1H-indole

HRID 1159782Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14].[CH2:22]([Sn](CCCC)(CCCC)C=C)[CH2:23]CC>C1(C)C=CC=CC=1>[CH3:12][O:11][C:9]1[CH:8]=[C:7]2[C:3]([CH:4]=[CH:5][N:6]2[S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[C:2]([CH:22]=[CH2:23])[CH:10]=1

Participants

Conditions

Temperature: 110 °C

Procedure

4-Bromo-6-methoxy-1-(phenylsulfonyl)-1H-indole (0.33 g, 0.9 mmol; Intermediate 32) was dissolved in dry toluene (4 mL) and tributyl(vinyl)stannane (0.53 mL, 1.8 mmol) and bis(triphenylphosphine)palladium(II)acetate (0.03 g, 0.05 mmol) were added. The mixture was stirred in STEM-block at 110° C. for 16 h. The crude product was combined with an earlier batch of this intermediate, filtrated and the solvent was evaporated. The residue was purified by flash chromatography using isohexane:dichloromethane 1:1 as eluent yielding 0.30 g (89%) of the title compound. MS (ESI+) for C17H15NO3S m/z 314 (M+H)+.

Workup

filtrationfiltrated
customthe solvent was evaporated
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-c652ddde589b4465896fcf28443085da
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812017B2

Reaction notes

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