2-(Tri-n-butylstannyl)thiophene → HCID 66974643, compound

HRID 1962629Notes

Reaction equation

C([Sn](CCCC)(CCCC)[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)CCC.[C:19]([O:23][C:24](=[O:43])[N:25]([CH2:27][C:28]1[CH:32]=[C:31](Br)[N:30]([S:34]([C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)(=[O:36])=[O:35])[CH:29]=1)[CH3:26])([CH3:22])([CH3:21])[CH3:20]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:26][N:25]([CH2:27][C:28]1[CH:32]=[C:31]([C:6]2[S:7][CH:8]=[CH:9][CH:10]=2)[N:30]([S:34]([C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)(=[O:36])=[O:35])[CH:29]=1)[C:24](=[O:43])[O:23][C:19]([CH3:22])([CH3:20])[CH3:21]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of crude tributyl(2-thienyl)stannane (1.1 g) and tert-butyl{[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (430 mg) in toluene was added tetrakis(triphenylphosphine)palladium (116 mg), and the mixture was stirred under a nitrogen atmosphere at 120° C. for 1 hr. The reaction mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=4:1) to give the title compound as a pale-yellow oil (yield 315 mg, 73%).

Workup

temperatureto cool to room temperature
customthe solvent was evaporated under reduced pressure
customThe residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=4:1)

Sources & evidence

ORD record: ord-225648cede264c8a835f1ff33fcc9fdb
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415368B2

Reaction notes

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