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

HRID 216328

반응식

HRID 216328 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 312751,4-Dioxane용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-43d217c3562947fcb3f9a7548c588cb2
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193228B2

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