Triethylborane → HCID 67078613, compound

HRID 1626005Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].C(B([CH2:12][CH3:13])CC)C.[Br:14][C:15]1[C:16](I)=[C:17]2[CH:23]=[CH:22][N:21]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:18]2=[N:19][CH:20]=1>CN(C)C=O>[Br:14][C:15]1[C:16]([CH2:12][CH3:13])=[C:17]2[CH:23]=[CH:22][N:21]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:25])=[O:26])[C:18]2=[N:19][CH:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride-dichloromethane complex (26 mg), potassium carbonate (130 mg) and triethylborane (1 M solution in hexane) (0.75 ml) were added to a solution of the compound obtained in Step 1 of Example 122 (300 mg) in N,N-dimethylformamide (12 ml). The mixture was stirred under nitrogen atmosphere at 80° C. for 24 hours. The reaction solution was cooled to room temperature and then separated by adding ethyl acetate and distilled water. The resulting organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane) to give the title compound (147 mg).

Workup

temperatureThe reaction solution was cooled to room temperature
customseparated
additionby adding ethyl acetate
distillationdistilled water
washThe resulting organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane)

Sources & evidence

ORD record: ord-2fdc0ea5cbde45908f24d4debc24c443
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785438B2

Reaction notes

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