Dichloromethane → HCID 58127393, 화합물

HRID 1963821노트

반응식

HRID 1963821 반응식
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

참가 물질

9

반응물 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

생성물 1

HCID 58127393HCID 58127393, 화합물수율 85.5%

시약·촉매·용매 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-342df9738c304193900732f9dee68a54
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415381B2

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