2-Bromopyridine → 1-(5-Fluoro-2,3'-bipyridin-6'-yl)ethanone

HRID 216328

反応式

HRID 216328 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Br[C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:17])[CH3:16])=[N:13][CH:14]=1.C[Sn](C)C.C[Sn](C)C.[F-:26].[K+]>O1CCOCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[F:26][C:5]1[CH:6]=[CH:7][C:2]([C:9]2[CH:14]=[N:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=2)=[N:3][CH:4]=1

参加物

7

反応物 4

HCID 79732-BromopyridineHCID 522689Potassium FluorideHCID 6327618HexamethylditinHCID 231453451-(5-Bromopyridin-2-yl)ethan-1-one

生成物 1

HCID 591620141-(5-Fluoro-2,3'-bipyridin-6'-yl)ethanone

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

Palladium tetrakis(triphenylphosphine) (289 mg, 0.25 mmol) was added to a degassed, ambient temperature solution of 2-bromopyridine (660 mg, 3.75 mmol), 1-(5-bromo-pyridin-2-yl)-ethanone (500 mg, 2.5 mmol) and hexamethylditin (1.2 g, 3.75 mmol) in degassed 1,4-dioxane (8 mL). After stirring at 110° C. overnight, the reaction mixture was cooled and KF/celite (1:1) was added. After stirring vigorously for 1 hr, reaction mixture was filtered and concentrated. Chromatography over silica eluting with 0-50% ethyl acetate/hexane afforded the title compound.

後処理

  1. temperaturethe reaction mixture was cooled
  2. stirringAfter stirring vigorously for 1 hr
  3. customreaction mixture
  4. filtrationwas filtered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-43d217c3562947fcb3f9a7548c588cb2
出典データセット
uspto-grants-2012_06
特許番号
US08193228B2

関連ノート

読み込み中…