Potassium Phosphate, Tribasic → HCID 86630866, compound

HRID 17522Notes

Reaction equation

HRID 17522 reaction equation
[NH2:1][C:2]1[C:3]([O:14][CH3:15])=[C:4]([CH:9]=[C:10](Br)[C:11]=1[F:12])[C:5]([O:7][CH3:8])=[O:6].[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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>[NH2:1][C:2]1[C:3]([O:14][CH3:15])=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=[C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]=1[F:12]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 86097491Methyl 3-amino-5-bromo-4-fluoro-2-methoxybenzoate

Product 1

HCID 86630866HCID 86630866, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 3-amino-5-bromo-4-fluoro-2-methoxybenzoate (I-230) (504 mg, 1.81 mmol) was dissolved in 1,4-dioxane (10 ml), then under nitrogen atmosphere at room temperature, phenylboronic acid (456 mg, 3.62 mmol), tripotassium phosphate (770 mg, 3.62 mmol) and tetrakis(triphenylphosphine)palladium(0) (210 mg, 0.18 mmol) were added. After stirred at 90° C. for 36 hours, this was cooled to room temperature. The insoluble matter was separated by filtration with washing with ethyl acetate, the filtrate was fractionated with ethyl acetate and saturated brine. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=3:1) to obtain the entitled compound (459 mg, 92%) as a colorless gel substance.

Workup

  1. temperaturethis was cooled to room temperature
  2. customThe insoluble matter was separated by filtration
  3. washwith washing with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated away
  7. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-6c025bd367a5442e9ddccfaa8551ec54
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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