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

HRID 72198

반응식

HRID 72198 반응식
[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]

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 1140Toluene용매HCID 10340Sodium Carbonate용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-d0fe431e8771484abd3fc46fec128397
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828991B2

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