Cesium carbonate → 1H-Pyrrolo[2,3-B]pyridine, 5-methyl-1-[(4-methylphenyl)sulfonyl]-

HRID 887369노트

반응식

HRID 887369 반응식
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1.[B-](F)(F)(F)[CH3:22].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.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]>[CH3:22][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 224773531H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[(4-methylphenyl)sulfonyl]-HCID 23692566Potassium Trifluoro(methyl)borate

생성물 1

HCID 497589241H-Pyrrolo[2,3-B]pyridine, 5-methyl-1-[(4-methylphenyl)sulfonyl]-수율 47%

시약·촉매·용매 3

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

실험 절차

A solution of 5-bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine (5 g, 14.29 mmol), potassium trifluoro(methyl)borate (2.62 g, 21.43 mmol), cesium carbonate (12.56 g, 38.57 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.16 g, 1.43 mmol) in THF (150 mL) and water (15 mL) was heated at reflux for 18 hours. The reaction mixture was cooled down to ambient and partitioned between EtOAc (100 mL) and water (100 mL). The organic phase was separated, washed with 1N HCl (100 mL) and brine (100 mL), then, dried over magnesium sulfate and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to give the title compound as a white solid (1.903 g, 47% yield).

후처리

  1. temperatureat reflux for 18 hours
  2. temperatureThe reaction mixture was cooled down to ambient and
  3. custompartitioned between EtOAc (100 mL) and water (100 mL)
  4. customThe organic phase was separated
  5. washwashed with 1N HCl (100 mL) and brine (100 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified on silica gel by flash column chromatography

출처 및 근거

ORD 기록
ord-ddbf5297d491402795fb18ed8450f792
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247421B2

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