Allyltributylstannane → 5-Allyl-4-(trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridine

HRID 2389896Notes

Reaction equation

Br[C:2]1[C:3]([Si:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]2[CH2:10][CH2:9][O:8][C:5]2=[N:6][CH:7]=1.[CH2:15]([Sn](CCCC)(CCCC)CCCC)[CH:16]=[CH2:17]>CN(C)C=O.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>[CH2:17]([C:2]1[C:3]([Si:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]2[CH2:10][CH2:9][O:8][C:5]2=[N:6][CH:7]=1)[CH:16]=[CH2:15]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-bromo-4-(trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridine (37.5 g, 138 mmol), allyltributyltin (65.8 mL, 212 mmol) and trans-dichlorobis(triphenylphosphine)palladium(II) (9.9 g, 14.1 mmol) in N,N-dimethylformamide (500 mL) was stirred at 100° C. for 1.5 hr. The reaction solution was diluted with water, and the mixture was extracted with diethyl ether. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=25/75→33/67) to give the title compound (30.9 g, yield 96%).

Workup

extractionthe mixture was extracted with diethyl ether
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=25/75→33/67)

Sources & evidence

ORD record: ord-ecc8b713d6234edca666a51dd8f6d88a
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273761B2

Reaction notes

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