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

HRID 2090753Notes

Reaction equation

C([Sn](CCCC)(CCCC)[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)CCC.Br[C:20]1[N:24]([S:25]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)(=[O:27])=[O:26])[CH:23]=[C:22]([CH2:34][N:35]([CH3:43])[C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH:21]=1>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>[CH3:43][N:35]([CH2:34][C:22]1[CH:21]=[C:20]([C:6]2[S:7][CH:8]=[CH:9][CH:10]=2)[N:24]([S:25]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)(=[O:27])=[O:26])[CH:23]=1)[C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:39])[CH3:40]

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-837bead33bb946678fe3af67d642633d
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436187B2

Reaction notes

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