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Water → 3'-Chloro-4'-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-biphenyl-4-carboxylic acid methyl ester

HRID 1095894
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HRID 1095894 반응식
[Cl:1][C:2]1[CH:3]=[C:4](OS(C(F)(F)F)(=O)=O)[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:22])[C:9]([C:15]1[CH:20]=[CH:19][N:18]=[C:17]([Cl:21])[CH:16]=1)([OH:14])[C:10]([F:13])([F:12])[F:11].[CH3:31][O:32][C:33]([C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1)=[O:34].O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C(OCC)(=O)C>[CH3:31][O:32][C:33]([C:35]1[CH:40]=[CH:39][C:38]([C:4]2[CH:5]=[CH:6][C:7]([CH:8]([CH3:22])[C:9]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([Cl:21])[CH:16]=3)([OH:14])[C:10]([F:11])([F:12])[F:13])=[C:2]([Cl:1])[CH:3]=2)=[CH:37][CH:36]=1)=[O:34]
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참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 86629107Trifluoro-methanesulfonic acid 3-chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenyl ester

생성물 1

HCID 469399523'-Chloro-4'-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-biphenyl-4-carboxylic acid methyl ester
수율 64%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
70 °C

실험 절차

Trifluoromethanesulfonic acid 3-chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenyl ester (Example 26, Step 1, 92 mg, 0.2 mmol), (4-methoxycarbonylphenyl)boronic acid (42 mg, 0.3 mmol) and 1,1,bis(diphenylphosphino)-ferrocenpalladium(II)dichloromethane (8 mg, 0.01 mmol) in dioxane (0.6 ml) was treated with water (0.44 ml) and 2N—Na2CO3 (0.3 ml, 0.6 mmol) and stirred at 70° C. under argon for 19 h. The reaction mixture was cooled down to r.t., diluted with ethyl acetate, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (10 g silica gel, heptane/AcOEt 4:1) to give the title compound as a white solid (62 mg). MS (m/e)=484.1 [M+H+].

후처리

  1. temperatureThe reaction mixture was cooled down to r.t.
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (10 g silica gel, heptane/AcOEt 4:1)

출처 및 근거

ORD 기록
ord-c11dabcd5e4a409f92d85bb93a0faa99
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08138189B2

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