Dichloromethane → HCID 68194460, compound

HRID 2370648Notes

Reaction equation

HRID 2370648 reaction equation
Br[C:2]1[C:3]([F:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[NH2:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+].ClCCl>C(COC)OC.O>[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:11]=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[C:3]=2[F:12])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27346154-Aminophenylboronic acidHCID 21584505Methyl 3-bromo-2-fluorobenzoate

Product 1

HCID 68194460HCID 68194460, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of Example 223A (3.1 g, 13 mmol) in dimethoxyethane (25 mL) was added (4-aminophenyl)boronic acid (2.77 g, 16 mmol) and Na2CO3 (3.38 g, 31.2 mmol) in water (6 mL) followed by 1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride:dichloromethane:complex (652 mg, 0.8 mmol). The mixture was heated to 85° C. for 10 hours. After cooling to room temperature, the reaction mixture was partitioned between water and ethyl acetate. The organic phase was washed with water followed by brine then dried over magnesium sulfate. After filtration and concentration, the crude product was purified by flash chromatography (1%-100% ethyl acetate/hexane) to provide the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between water and ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialthen dried over magnesium sulfate
  5. filtrationAfter filtration and concentration
  6. customthe crude product was purified by flash chromatography (1%-100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4af63ec729424a6c83bc2e0da4932835
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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