Water → 4-Amino-4'-chlorobiphenyl-3-carboxylic acid methyl ester

HRID 72198

Reaction equation

HRID 72198 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8](Br)[CH:7]=[CH:6][C:5]=1[NH2:11].[Cl:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(OCC)(=O)C.O>C1(C)C=CC=CC=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+].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>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]([C:17]2[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=2)[CH:7]=[CH:6][C:5]=1[NH2:11])=[O:12]

Participants

9

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 742994-Chlorophenylboronic acidHCID 736224Methyl 2-amino-5-bromobenzoate

Product 1

HCID 689796924-Amino-4'-chlorobiphenyl-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of 2-amino-5-bromobenzoic acid methyl ester (460.1 mg) in degassed toluene was mixed with tetrakis(triphenylphosphine)palladium (0) (62.4 mg) and stirred at room temperature for 10 min. Then 4-chlorophenylboronic acid (344 mg) in ethanol (0.76 mL) and 2 M sodium carbonate solution (1.34 mL) were added, and the reaction mixture was heated at 100° C. overnight. The reaction was then mixed with ethyl acetate and water. The aqueous phase was extracted several times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The crude product was purified by preparative HPLC. The product with the molecular weight of 261.71 (C14H12ClNO2) was obtained in this way; MS (ESI): 262 (M+H+).

Workup

  1. temperaturethe reaction mixture was heated at 100° C. overnight
  2. extractionThe aqueous phase was extracted several times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by preparative HPLC
  6. customThe product with the molecular weight of 261.71 (C14H12ClNO2) was obtained in this way

Sources & evidence

ORD record
ord-d0fe431e8771484abd3fc46fec128397
Source dataset
uspto-grants-2014_09
Patent number
US08828991B2

Linked notes

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