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

HRID 426357노트

반응식

HRID 426357 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
95 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4aa7ff390f9d42c883af2eb5b8cdd0b3
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106236B2

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