Triethylamine → HCID 59186923, compound

HRID 1947237Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][C:8]=1[O:15][CH3:16])(=O)=O.[C:19]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])(=[O:22])[CH:20]=[CH2:21].C(N(CC)CC)C>CN(C=O)C.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>[C:13]([C:10]1[CH:11]=[CH:12][C:7](/[CH:21]=[CH:20]/[C:19]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[C:8]([O:15][CH3:16])[CH:9]=1)#[N:14]

Participants

Conditions

Temperature: 100 °C

Procedure

4 g (5.7 mmol) of bis(triphenylphosphine)palladium(II) chloride are added to a degassed solution of 37.13 g (132 mmol) of 4-cyano-2-methoxyphenyl trifluoromethanesulfonate, 35 ml (245 mmol) of tert-butyl acrylate and 90 ml (645 mmol) of triethylamine in DMF (250 ml). The solution is stirred at 100° C. under a protective gas atmosphere for 24 h. Ice-water (1000 ml) is then added, and the suspension is extracted with ethyl acetate (3×100 ml). The organic phase is washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated. The residue is purified by column chromatography (silica gel, mobile phase:cyclohexane/ethyl acetate 10:1). 24.6 g (72% of theory) of the title compound are obtained as a white solid.

Workup

extractionthe suspension is extracted with ethyl acetate (3×100 ml)
washThe organic phase is washed with saturated sodium chloride solution
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue is purified by column chromatography (silica gel, mobile phase:cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record: ord-e330c8b51a1b48f3b98e2e6620a15bb3
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399471B2

Reaction notes

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