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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
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HRID 1945316 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-217096ef447c4e4baed7ac08e2efd5ce
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08394969B2

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