Triethylamine → HCID 67772403, compound

HRID 533397Notes

Reaction equation

FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=2)[CH:10]=[CH:9][N:8]=1)(=O)=O.[F:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([F:31])[C:25]=1OB(O)O.C(N(CC)CC)C.O1CCOCC1>O.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>[F:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([F:31])[C:25]=1[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=2)[CH:10]=[CH:9][N:8]=1

Participants

Conditions

Temperature: 95 °C

Procedure

Under argon gas atmosphere, a mixture of methyl 1-{[(trifluoromethyl)sulfonyl]oxy}isoquinoline-7-carboxylate (250 mg), 2,4,6-trifluorophenylboric acid (184 mg), tetrakis(triphenylphosphine)palladium (22 mg), triethylamine (189 mg), and 1,4-dioxane (15 mL) was heated under stirring in an oil bath at 95° C. for 18 hours. The reaction mixture was returned to room temperature, diluted with water, and then extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate) to obtain methyl 1-(2,4,6-trifluorophenyl)isoquinoline-7-carboxylate (228 mg).

Workup

temperaturewas heated
customwas returned to room temperature
extractionextracted with ethyl acetate
concentrationThe organic layer was concentrated under reduced pressure
customthe resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-61aff2d9117e4425980b9a5dac64140d
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853242B2

Reaction notes

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