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

HRID 2091766
ノート
印刷プレビュー

反応式

HRID 2091766 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 178418397
HCID 178418397、化合物
触媒
HCID 702Ethanol溶媒
HCID 962Water溶媒
HCID 1140Toluene溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

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%)

後処理

  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)

出典と根拠

ORDレコード
ord-0b285860211d4c01bd4537944af2d699
出典データセット
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08440657B2

反応ノート

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