Stannane, tributyl(1-ethoxyethenyl)- → 1-(5-Methyl-1H-pyrazolo[3,4-c]pyridin-3-yl)-ethanone

HRID 1527270노트

반응식

HRID 1527270 반응식
Br[C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([CH3:11])[CH:9]=2)[NH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:17]([O:19]CC)=[CH2:18])CCC>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:11][C:8]1[CH:9]=[C:10]2[C:2]([C:17](=[O:19])[CH3:18])=[N:3][NH:4][C:5]2=[CH:6][N:7]=1

참가 물질

5

반응물 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 178421791HCID 178421791, 화합물

생성물 1

HCID 682840311-(5-Methyl-1H-pyrazolo[3,4-c]pyridin-3-yl)-ethanone

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

A solution of 3-bromo-5-methyl-1H-pyrazolo[3,4-c]pyridine (2.13 g, 10.04 mmol), tri-butyl(1-ethoxyvinyl)tin (6.78 mL, 20.09 mmol) and PdCl2(PPh3)2 (0.705 mg, 1 mmol) in DMF (12.6 mL) was heated at 80° C. overnight under argon atmosphere. Then concentrated under reduced pressure and diluted with EtOAc. HCl (2N) was added, the layers were separated and the aqueous layer was basified by addition of NaHCO3 (1N in water) and extracted with EtOAc (3×). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The yellow oil thus obtained was used without further purification in the next step. TLC, Rf (c-hexane/EtOAC 1:1)=0.05; MS (UPLC/MS): 176 [M+H]+, 174 [M−H]−.

후처리

  1. concentrationThen concentrated under reduced pressure
  2. additiondiluted with EtOAc
  3. additionHCl (2N) was added
  4. customthe layers were separated
  5. additionthe aqueous layer was basified by addition of NaHCO3 (1N in water)
  6. extractionextracted with EtOAc (3×)
  7. dry with materialThe combined organic extracts were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe yellow oil thus obtained
  11. customwas used without further purification in the next step

출처 및 근거

ORD 기록
ord-64de0387def442e2af14790bfd63a406
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085555B2

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