Potassium Carbonate → (2'-Formyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

HRID 456235

반응식

HRID 456235 반응식
Br[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:14][O:15][C:16](=[O:35])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20](B2OC(C)(C)C(C)(C)O2)[CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C(Cl)Cl.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>[CH3:14][O:15][C:16](=[O:35])[CH2:17][C:18]1[CH:19]=[C:20]([C:2]2[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=2[CH:4]=[O:5])[C:21]([O:24][CH3:25])=[CH:22][CH:23]=1

참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 70180472-Bromo-5-(trifluoromethyl)benzaldehydeHCID 57576289Methyl 2-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)acetate

생성물 1

HCID 86633167(2'-Formyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 6344Dichloromethane용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
90 °C

실험 절차

2-Bromo-5-trifluoromethyl-benzaldehyde (4.152 g, 16.4 mmol), [4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid methyl ester (4.988 g, 16.41 mmol), and potassium carbonate (5.67 g, 41.03 mmol) were combined in DME (40 mL) and H2O (20 mL) under N2. The mixture was purged with N2, and then tetrakis(triphenylphosphine)palladium(0) (1.9 g, 1.64 mmol) was added, and the reaction was heated to 90° C. for 10 hours. Once no starting material was seen by analytical LCMS, the mixture was cooled to room temperature and diluted with CH2Cl2 and H2O. The aqueous layer was separated and extracted with CH2Cl2, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give the title compound.

후처리

  1. customThe mixture was purged with N2
  2. temperaturethe mixture was cooled to room temperature
  3. customThe aqueous layer was separated
  4. extractionextracted with CH2Cl2
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-b090a18425a143bca5844a1ad6ee0c36
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497381B2

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