4-Fluorophenylboronic acid → HCID 24987225, compound

HRID 216625Notes

Reaction equation

HRID 216625 reaction equation
[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]2[C:12]([C:13]=1[C:14]([NH2:16])=[O:15])=[CH:11][CH:10]=[C:9](Br)[CH:8]=2)=[O:3].C(=O)([O-])O.[Na+].[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1>O.O1CCOCC1.[Cl-].[Na+].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>[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]2[C:12]([C:13]=1[C:14]([NH2:16])=[O:15])=[CH:11][CH:10]=[C:9]([C:27]1[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=1)[CH:8]=2)=[O:3]

Participants

8

Reactant 3

HCID 2856454-Fluorophenylboronic acidHCID 516892Sodium BicarbonateHCID 24987222HCID 24987222, compound2×

Product 1

HCID 24987225HCID 24987225, compoundYield 49.8%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

A solution mixture of 2-aminocarbonylamino-6-bromoindole-3-carboxamide (Compound 3-1, 80 mg, 0.27 mmol), sodium hydrogen carbonate (57 mg, 0.68 mmol), 4-fluorophenylboronic acid (57 mg, 0.41 mmol) and tetrakis(triphenylphosphine)palladium (0) (16 mg, 0.014 mmol) in water and 1,4-dioxane (water/1,4-dioxane=1/3, 15 mL) was stirred at 100° C. for 1.5 hours. Brine (5 mL) was added to the reaction mixture, and the whole was extracted with ethyl acetate (5 mL). The organic layer was dried over anhydrous magnesium sulfate and filtered throught Celite® pad. After the solvent was evaporated under reduced pressure, the resultant solid was washed with a solution mixture of methanol and diethyl ether (methanol/diethyl ether=1/10, 2 mL), and dried under reduced pressure to give the title compound (42 mg) as slightly brown solid (yield 51%).

Workup

  1. extractionthe whole was extracted with ethyl acetate (5 mL)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customAfter the solvent was evaporated under reduced pressure
  5. washthe resultant solid was washed with a solution mixture of methanol and diethyl ether (methanol/diethyl ether=1/10, 2 mL)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-ab5adb750f734b71baca268855812631
Source dataset
uspto-grants-2012_06
Patent number
US08193237B2

Reaction notes

Loading…