Potassium Carbonate → 2-Phenylpyridine

HRID 1400190ノート

反応式

HRID 1400190 の反応式
Cl[C:2]1[C:7](CCC(O)=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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>[C:13]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 866427913-(2-chloropyridin-3-yl)propanoic acid

生成物 1

HCID 138872-Phenylpyridine収率 91%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

Pd(PPh3)4 (3.0 g, 2.6 mmol) was added to a solution of 2-chloro-3-carboxyethylpyridine (25 g, 134.7 mmol), phenylboronic acid (21.04 g, 172.6 mmol) and K2CO3 (55.1 g, 399 mmol) in 1,4-dioxane (200 mL) and water (200 mL). The reaction mixture was heated at 100° C. for 2 h. The solution was then cooled to room temperature and the dioxane was removed under reduced pressure. The resulting aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried (Na2SO4), filtered through celite, and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 10-100% EtOAc/hexanes) to get the 2-phenylpyridine derivative in 91% yield (27.98 g). LC-MS Rt (retention time): 2.45 min, MS: (ES) m/z 228 (M+H+).

後処理

  1. temperatureThe solution was then cooled to room temperature
  2. customthe dioxane was removed under reduced pressure
  3. extractionThe resulting aqueous layer was extracted with ethyl acetate
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered through celite
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (SiO2, 10-100% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-7f1e12917c374963b11a21b22f3c90c9
出典データセット
uspto-grants-2014_12
特許番号
US08906938B2

反応ノート

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