Tributylvinyltin → methyl 3-cyclohexyl-2-vinyl-1H-indole-6-carboxylate

HRID 1713940Notes

Reaction equation

Br[C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2.[CH2:21]([Sn](CCCC)(CCCC)C=C)[CH2:22]CC>O1CCOCC1.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:11]1([C:10]2[C:9]3[C:4](=[CH:5][C:6]([C:17]([O:19][CH3:20])=[O:18])=[CH:7][CH:8]=3)[NH:3][C:2]=2[CH:21]=[CH2:22])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (from Example 1, Step 3) in dioxane (0.15 M) was added tri-n-butyl vinyl tin (1.1 eq.) followed by bis(triphenylphosphine)palladium(II) chloride (0.1 eq.). The reaction was stirred under nitrogen at 100° C. for 3 h and then cooled to RT. The mixture was then diluted with EtOAc and washed with brine (3×). The organic phase was then dried over Na2SO4 and evaporated to dryness. The residual material was purified by chromatography on silica gel (PE:EtOAc, 9:1). The product fractions were evaporated and the residual material re-crystallised from DCM with PE. The product was obtained as yellow crystalline material (60%).

Workup

temperaturecooled to RT
washwashed with brine (3×)
dry with materialThe organic phase was then dried over Na2SO4
customevaporated to dryness
customThe residual material was purified by chromatography on silica gel (PE:EtOAc, 9:1)
customThe product fractions were evaporated
customthe residual material re-crystallised from DCM with PE

Sources & evidence

ORD record: ord-a20cd07590284cc5aa433bf5c485bc5d
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795250B2

Reaction notes

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