Dichloromethane → HCID 58127393、化合物

HRID 1623240ノート

反応式

HRID 1623240 の反応式
FC(F)(F)S(O[C:7]1[C:12]([F:13])=[CH:11][CH:10]=[C:9]([F:14])[N:8]=1)(=O)=O.[Cl:17][C:18]1[C:19](B(O)O)=[CH:20][C:21]([F:24])=[N:22][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>C1COCC1.CCOC(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]>[Cl:17][C:18]1[C:19]([C:7]2[C:12]([F:13])=[CH:11][CH:10]=[C:9]([F:14])[N:8]=2)=[CH:20][C:21]([F:24])=[N:22][CH:23]=1

参加物

9

反応物 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 44754822(5-Chloro-2-fluoropyridin-4-yl)boronic acidHCID 86650604Methanesulfonic acid, 1,1,1-trifluoro-, 3,6-difluoro-2-pyridinyl ester

生成物 1

HCID 58127393HCID 58127393、化合物収率 85.5%

試薬・触媒・溶媒 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of 3,6-difluoropyridin-2-yl trifluoromethanesulfonate (3.50 g, 13.30 mmol) and 5-chloro-2-fluoropyridine-4-boronic acid (3.27 g, 18.62 mmol) in THF (27 ml) was degassed by bubbling Argon gas for 10 min. Aqueous sodium carbonate (13.30 ml, 26.6 mmol) and PdCl2(dppf).CH2Cl2 adduct (0.652 g, 0.798 mmol) were added, and the mixture was degassed for an additional 5 min. The resulting reaction mixture was stirred at about 100° C. for 2 hr in a sealed vessel. The reaction mixture was cooled to ambient temperature, diluted with EtOAc and water. The separated organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue was purified by column chromatography over silica gel (heptanes/ethyl acetate gradient) to yield 2.78 g (85% yield) of 5′-chloro-2′,3,6-trifluoro-2,4′-bipyridine as a crystalline solid. LCMS (m/z): 244.9 [M+H]+; retention time=0.86 min.

後処理

  1. customwas degassed
  2. customby bubbling Argon gas for 10 min
  3. customthe mixture was degassed for an additional 5 min
  4. customThe resulting reaction mixture
  5. temperatureThe reaction mixture was cooled to ambient temperature
  6. dry with materialThe separated organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified by column chromatography over silica gel (heptanes/ethyl acetate gradient)

出典と根拠

ORDレコード
ord-deaa685021424da79315e0860e7f6771
出典データセット
uspto-grants-2014_07
特許番号
US08778951B2

反応ノート

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