Toluene → HCID 67775631, compound

HRID 533426Notes

Reaction equation

HRID 533426 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[C:5]([C:16]2[C:21]([F:22])=[CH:20][C:19]([F:23])=[CH:18][C:17]=2[F:24])=[N:4][CH:3]=1.[CH2:25](B(O)O)[CH3:26].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>O.C(OCC)(=O)C.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>[CH2:25]([C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[C:5]([C:16]2[C:21]([F:22])=[CH:20][C:19]([F:23])=[CH:18][C:17]=2[F:24])=[N:4][CH:3]=1)[CH3:26]

Participants

8

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 521157Ethylboronic acidHCID 67773046HCID 67773046, compound

Product 1

HCID 67775631HCID 67775631, compoundYield 54.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Under argon gas atmosphere, a mixture of methyl 4-bromo-1-(2,4,6-trifluorophenyl)isoquinoline-7-carboxylate (150 mg), ethylboronic acid (84 mg), tetrakis(triphenylphosphine)palladium (44 mg), tripotassium phosphate (241 mg), toluene (5 mL), and water (0.3 mL) was heated under stirring in an oil bath at 100° C. for one day. The reaction mixture was returned to room temperature, and diluted with water and ethyl acetate, and then the insoluble matter was separated by filtration. The filtrate was extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate) to obtain methyl 4-ethyl-1-(2,4,6-trifluorophenyl)isoquinoline-7-carboxylate (71 mg).

Workup

  1. temperaturewas heated
  2. customwas returned to room temperature
  3. customthe insoluble matter was separated by filtration
  4. extractionThe filtrate was extracted with ethyl acetate
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customThe resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e4f708e2e10d48a5ae7c66edb48efee1
Source dataset
uspto-grants-2014_10
Patent number
US08853242B2

Reaction notes

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