Cesium carbonate → 5-(6-chloropyridin-3-yl)-1-ethylpyridin-2(1H)-one

HRID 1925169ノート

反応式

HRID 1925169 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5](=[O:10])[N:6]([CH2:8][CH3:9])[CH:7]=1.[Cl:11][C:12]1[N:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C([O-])([O-])=O.[Cs+].[Cs+]>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>[Cl:11][C:12]1[N:17]=[CH:16][C:15]([C:2]2[CH:3]=[CH:4][C:5](=[O:10])[N:6]([CH2:8][CH3:9])[CH:7]=2)=[CH:14][CH:13]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 38450342-Chloropyridine-5-boronic acidHCID 122105365-Bromo-1-ethylpyridin-2(1H)-one

生成物 1

HCID 592332885-(6-chloropyridin-3-yl)-1-ethylpyridin-2(1H)-one収率 54.1%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
140 °C

実験手順

A mixture of 5-bromo-1-ethylpyridin-2(1 H)-one (1.9 g, 9.45 mmol), 6-chloropyridin-3-ylboronic acid (1.8 g, 11.46 mmol), Cs2CO3 (9.9 g, 30.37 mmol) and tetrakis(triphenylphosphine)palladium (0) (543 mg, 0.55 mmol) were suspended in dioxane:water (15:1, 20 ml). After degassing, the mixture was heated in a microwave at 140° C. for 30 min. The reaction was then diluted with EtOAc and washed with water. The organic layer was dried over Na2SO4, filtered, and concentrated to dryness via rotary evaporation. The resulting residue was purified by LCMS to provide the title compound, 5-(6-chloropyridin-3-yl)-1-ethylpyridin-2(1 H)-one (1.2 g, 51% yield).

後処理

  1. customAfter degassing
  2. additionThe reaction was then diluted with EtOAc
  3. washwashed with water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness via rotary evaporation
  7. customThe resulting residue was purified by LCMS

出典と根拠

ORDレコード
ord-2be1bd6f38564219b32c7cb50da8b1d3
出典データセット
uspto-grants-2012_05
特許番号
US08178534B2

反応ノート

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