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

HRID 72198

反応式

HRID 72198 の反応式
[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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒HCID 10340Sodium Carbonate溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-d0fe431e8771484abd3fc46fec128397
出典データセット
uspto-grants-2014_09
特許番号
US08828991B2

関連ノート

読み込み中…