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Methyl 5-hydroxy-2-methylbenzoate → 5-(5-Biphenyl-4-yl-6-fluoro-1H-benzoimidazol-2-yloxy)-2-methyl-benzoic acid methyl ester

HRID 1945316
ノート
印刷プレビュー

反応式

HRID 1945316 の反応式
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:19]([F:20])=[CH:18][C:10]3[NH:11][C:12](S(C)(=O)=O)=[N:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1.[CH3:27][O:28][C:29](=[O:38])[C:30]1[CH:35]=[C:34]([OH:36])[CH:33]=[CH:32][C:31]=1[CH3:37]>N1C=CC=CC=1.CCOC(C)=O>[CH3:27][O:28][C:29](=[O:38])[C:30]1[CH:35]=[C:34]([O:36][C:12]2[NH:11][C:10]3[CH:18]=[C:19]([F:20])[C:7]([C:4]4[CH:5]=[CH:6][C:1]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)=[CH:2][CH:3]=4)=[CH:8][C:9]=3[N:13]=2)[CH:33]=[CH:32][C:31]=1[CH3:37]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 13929055Methyl 5-hydroxy-2-methylbenzoateHCID 674455365-Biphenyl-4-yl-6-fluoro-2-methanesulfonyl-1H-benzoimidazole

生成物 1

HCID 685244605-(5-Biphenyl-4-yl-6-fluoro-1H-benzoimidazol-2-yloxy)-2-methyl-benzoic acid methyl ester

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 7 (454 mg, 1.2 mmol) in pyridine 10 mL was added 5-hydroxy-2-methyl-benzoic acid methyl ester (412 mg, 2.4 mmol). The reaction mixture was heated to reflux for 5 days. Once the reaction was determined to be complete by TLC, the reaction mixture was diluted with EtOAc (100 mL) and washed two times with 100 mL portions of saturated aqueous ammonium chloride. The combined organic layers were dried over MgSO4 filtered and concentrated in vacuo to give a crude brown oil. The resulting oil was purified on ISCO (EtOAc/Hexanes=2/3) to give title compound 8 as a yellow oil.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 days
  3. washwashed two times with 100 mL portions of saturated aqueous ammonium chloride
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a crude brown oil
  8. customThe resulting oil was purified on ISCO (EtOAc/Hexanes=2/3)

出典と根拠

ORDレコード
ord-217096ef447c4e4baed7ac08e2efd5ce
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08394969B2

反応ノート

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