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Sodium Carbonate → 2,2,2-Trifluoro-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanone

HRID 216334
ノート
印刷プレビュー

反応式

HRID 216334 の反応式
[F:1][C:2]([F:21])([F:20])[C:3]([C:5]1[CH:10]=[CH:9][C:8](B2OC(C)(C)C(C)(C)O2)=[CH:7][CH:6]=1)=[O:4].Br[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:21][C:2]([F:1])([F:20])[C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=2)=[CH:9][CH:10]=1)=[O:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 27831712-Bromo-5-fluoropyridineHCID 569730602,2,2-Trifluoro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethan-1-one

生成物 1

HCID 591619282,2,2-Trifluoro-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanone

試薬・触媒・溶媒 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒
HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

Pd(dppf)Cl2 (2.5 g, 3.3 mmol) was added to a degassed, ambient temperature solution of 2,2,2-trifluoro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanone (20 g, 67 mmol), 2-bromo-5-fluoropyridine (11.6 g, 67 mmol) and sodium carbonate (12.7 g, 134 mmol) in N,N-dimethylformamide (4400 mL) and water (90 mL). After heating at 90° C. overnight, the reaction mixture was poured into ice (400 g) and extracted with diethyl ether. The combined organic extracts were dried (magnesium sulfate), filtered and concentrated in vacuo. Chromatography over silica eluting with petroleum ether/ethyl acetate (20:1) afforded the title compound.

後処理

  1. extractionextracted with diethyl ether
  2. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-b30d3b8e4fcc46e4a25fd3fdda072028
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08193228B2

反応ノート

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