Sodium Carbonate → HCID 178517107, compound

HRID 1845975Notes

Reaction equation

HRID 1845975 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:3]=1[C:4]([O:6]C)=O.CC1(C)C(C)(C)OB([C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[NH2:23])O1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[F:12][C:9]1[CH:10]=[CH:11][C:2]2[C:3](=[C:4]([OH:6])[N:23]=[C:22]3[C:24]=2[CH:25]=[CH:26][CH:27]=[CH:21]3)[CH:8]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 138875Benzoic acid, 2-bromo-5-fluoro-, methyl esterHCID 27346522-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 178517107HCID 178517107, compoundYield 65.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2-bromo-5-fluorobenzoate (0.250 g, 1.07 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.235 g, 1.07 mmol), palladium acetate (2.4 mg, 0.01 eq.), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (8.81 mg, 0.021 mmol), and sodium carbonate (0.114 g, 1.073 mmol) in ethanol (5.4 mL) was heated to 80° C. for 3 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was triturated with hexane, and isolated by vacuum filtration, washed with water, and dried to provide the title compound (0.15 g, 65% yield) which was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was triturated with hexane
  4. customisolated by vacuum filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-f0964649d1874821a3cc4653da2934ea
Source dataset
uspto-grants-2015_02
Patent number
US08951964B2

Reaction notes

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