1,2-Dimethoxyethane → 4-Methyl-2-(3,5,3'',5''-tetrafluoro-[1,1';3',1'']terphenyl-5'-yl)-pentanoic acid methyl ester

HRID 426357ノート

反応式

HRID 426357 の反応式
[CH3:1][O:2][C:3](=[O:31])[CH:4]([C:9]1[CH:14]=[C:13](OS(C(F)(F)F)(=O)=O)[CH:12]=[C:11](OS(C(F)(F)F)(=O)=O)[CH:10]=1)[CH2:5][CH:6]([CH3:8])[CH3:7].[F:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[C:37]([F:39])[CH:38]=1.C([O-])([O-])=O.[K+].[K+].CO[CH2:51][CH2:52]OC>CCOC(C)=O.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](=[O:31])[CH:4]([C:9]1[CH:10]=[C:11]([C:52]2[CH:51]=[C:37]([F:39])[CH:38]=[C:33]([F:32])[CH:34]=2)[CH:12]=[C:13]([C:35]2[CH:34]=[C:33]([F:32])[CH:38]=[C:37]([F:39])[CH:36]=2)[CH:14]=1)[CH2:5][CH:6]([CH3:7])[CH3:8]

参加物

7

反応物 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 590047892-(3,5-Bis-trifluoromethanesulfonyloxy-phenyl)-4-methyl-pentanoic acid methyl ester

生成物 1

HCID 590047714-Methyl-2-(3,5,3'',5''-tetrafluoro-[1,1';3',1'']terphenyl-5'-yl)-pentanoic acid methyl ester

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
95 °C

実験手順

A mixture of 2-(3,5-bis-trifluoromethanesulfonyloxy-phenyl)-4-methyl-pentanoic acid methyl ester (104 mg, 0.21 mmol), 3,5-difluorophenylboronic acid (82 mg, 0.52 mmol), K2CO3 solution (2M, 310 μL) and DME (2 mL) was purged with N2 three times before adding Pd(PPh3)4 (10 mg, 0.01 mmol). The mixture was heated at 95° C. overnight (followed by HPLC). The reaction was diluted with EtOAc (5 mL) and then washed successively with NaHCO3 solution and brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give the title compound as an oil. The residue was purified by flash chromatography (0-15% EtOAc in Petroleum ether) to give the title compound (75 mg, 84%) as a yellow oil.

後処理

  1. customwas purged with N2 three times
  2. washwashed successively with NaHCO3 solution and brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4aa7ff390f9d42c883af2eb5b8cdd0b3
出典データセット
uspto-grants-2012_01
特許番号
US08106236B2

反応ノート

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