Cesium fluoride → Acetic acid 6-(4-methanesulfonyl-3-methoxy-phenyl)-5-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-yl ester

HRID 748946ノート

反応式

HRID 748946 の反応式
C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[F-].[Cs+].[N:22]1([CH2:28][CH2:29][O:30][C:31]2[CH:59]=[CH:58][C:34]([O:35][C:36]3[C:45](OS(C(F)(F)F)(=O)=O)=[CH:44][CH:43]=[C:42]4[C:37]=3[CH:38]=[CH:39][C:40]([O:54][C:55](=[O:57])[CH3:56])=[CH:41]4)=[CH:33][CH:32]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.B1(B2OCC(C)(C)CO2)OCC(C)(C)CO1.[CH3:76][S:77]([C:80]1[CH:85]=[CH:84][C:83](OS(C(F)(F)F)(=O)=O)=[CH:82][C:81]=1[O:94][CH3:95])(=[O:79])=[O:78]>CC#N.CC([O-])=O.CC([O-])=O.[Pd+2].O>[CH3:76][S:77]([C:80]1[CH:85]=[CH:84][C:83]([C:45]2[C:36]([O:35][C:34]3[CH:58]=[CH:59][C:31]([O:30][CH2:29][CH2:28][N:22]4[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]4)=[CH:32][CH:33]=3)=[C:37]3[C:42](=[CH:43][CH:44]=2)[CH:41]=[C:40]([O:54][C:55](=[O:57])[CH3:56])[CH:39]=[CH:38]3)=[CH:82][C:81]=1[O:94][CH3:95])(=[O:79])=[O:78]

参加物

9

反応物 5

HCID 25953Cesium fluorideHCID 75806TricyclohexylphosphineHCID 2734316Bis(neopentyl glycolato)diboronHCID 583385445-(4-(2-(Piperidin-1-yl)ethoxy)phenoxy)-6-(trifluoromethylsulfonyloxy)naphthalen-2-yl acetateHCID 86607165Trifluoro-methanesulfonic acid 4-methanesulfonyl-3-methoxy-phenyl ester

生成物 1

HCID 59751425Acetic acid 6-(4-methanesulfonyl-3-methoxy-phenyl)-5-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-yl ester収率 33%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
90 °C

実験手順

Combine Pd(OAc)2 (46 mg, 0.20 mmol), tricyclohexylphosphine (95 mg, 0.34 mmol), and CsF (1.85 g, 12.26 mmol) in CH3CN (20 mL) under N2. Stir the reaction mixture for 5 minutes. Add acetic acid 5-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-6-trifluoromethanesulfonyloxy-naphthalen-2-yl ester (730 mg, 1.36 mmol) and bis(neopentyl glycolato)diboron (460 mg, 2.04 mmol) to the reaction mixture. Heat to 90° C. and stir for about 5 minutes. Add trifluoro-methanesulfonic acid 4-methanesulfonyl-3-methoxy-phenyl ester (500 mg, 1.5 mmol) and continue to heat the mixture for two hours. Cool to room temperature, add water (100 mL), and extract the aqueous layer with CH2Cl2 (3×100 mL). Combine the organic layers and dry with Na2SO4, filter and concentrate. Purify by flash column chromatography (silica gel, 0 to 5% MeOH/CH2Cl2) to give 260 mg of the title compound (33%): mass spectrum: (ion spray): m/z=590.4 (M+H).

後処理

  1. stirringstir for about 5 minutes
  2. temperatureto heat the mixture for two hours
  3. temperatureCool to room temperature
  4. extractionextract the aqueous layer with CH2Cl2 (3×100 mL)
  5. dry with materialCombine the organic layers and dry with Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify by flash column chromatography (silica gel, 0 to 5% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-f248bac41f634d08856ae6e60d196386
出典データセット
uspto-grants-2008_07
特許番号
US07399867B2

反応ノート

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