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Potassium Carbonate → Methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]nicotinate

HRID 2091766
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HRID 2091766 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.Cl.[CH3:14][O:15][C:16]([C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[N:22][CH:23]=1)=[O:17].C(=O)([O-])[O-].[K+].[K+].[F-].[K+]>C1(C)C=CC=CC=1.C(O)C.O.C(OCC)(=O)C.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>[F:10][C:9]([F:12])([F:11])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:20]2[CH:21]=[N:22][CH:23]=[C:18]([CH:19]=2)[C:16]([O:15][CH3:14])=[O:17])=[CH:3][CH:4]=1
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참가 물질

10

반응물 4

HCID 11430Potassium CarbonateHCID 522689Potassium FluorideHCID 100829441-Bromo-4-(2,2,2-trifluoroethyl)benzeneHCID 66890177[5-(Methoxycarbonyl)pyridin-3-yl]boronic acid hydrochloride

생성물 1

HCID 58116526Methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]nicotinate

시약·촉매·용매 5

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 702Ethanol용매
HCID 962Water용매
HCID 1140Toluene용매
HCID 8857Ethyl Acetate용매

실험 절차

A solution of 8.00 g (33.5 mmol) of the compound from Example 40A in toluene (304 ml) was admixed under argon at RT with 10.9 g (50.2 mmol) of the compound from Example 33A in ethanol (100 ml) and 5.10 g (36.8 mmol) of potassium carbonate. After stirring for 10 min, 3.87 g (3.35 mmol) of tetrakis(triphenylphosphine)palladium and then 5.83 g (100 mmol) of potassium fluoride in water (64 ml) were added. The mixture was stirred under reflux for 8 h, and the reaction solution was cooled and diluted with ethyl acetate. The reaction solution was washed in water, and the organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by means of column chromatography (silica gel, dichloromethane/methanol 100:1→80:1). Yield: 9.20 g (69% of theory, purity 75%)

후처리

  1. stirringThe mixture was stirred
  2. temperatureunder reflux for 8 h
  3. temperaturethe reaction solution was cooled
  4. washThe reaction solution was washed in water
  5. dry with materialthe organic phase was dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by means of column chromatography (silica gel, dichloromethane/methanol 100:1→80:1)

출처 및 근거

ORD 기록
ord-0b285860211d4c01bd4537944af2d699
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08440657B2

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