Sodium Carbonate → HCID 67773073, compound

HRID 533400Notes

Reaction equation

HRID 533400 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14]C)=[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.[CH3:25]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>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>[CH3:25][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=2)[C:5]([C:16]2[C:17]([F:24])=[CH:18][C:19]([F:23])=[CH:20][C:21]=2[F:22])=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 574072TrimethylboroxineHCID 67773046HCID 67773046, compound

Product 1

HCID 67773073HCID 67773073, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 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 (160 mg), trimethylboroxin (117 mg), tetrakis(triphenylphosphine)palladium (23 mg), 2M aqueous sodium carbonate solution (1 mL), and 1,4-dioxane (5 mL) was heated under stirring in an oil bath at 100° C. for 4 hours. The reaction mixture was returned to room temperature and diluted with ethyl acetate, and then the insoluble materials were separated by filtration through Celite. The filtrate was 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 4-methyl-1-(2,4,6-trifluorophenyl)isoquinoline-7-carboxylic acid (95 mg).

Workup

  1. temperaturewas heated
  2. customwas returned to room temperature
  3. customthe insoluble materials were separated by filtration through Celite
  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-3622e2d0f14647e196c48b1bca1df273
Source dataset
uspto-grants-2014_10
Patent number
US08853242B2

Reaction notes

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