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Triethylamine → HCID 67772403, compound

HRID 533397
Notes
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Reaction equation

HRID 533397 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 22237819HCID 22237819, compoundHCID 86666250HCID 86666250, compound

Product 1

HCID 67772403HCID 67772403, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent

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

  1. temperaturewas heated
  2. customwas returned to room temperature
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes