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

HRID 1527270Notes

Reaction equation

HRID 1527270 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

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]−.

Workup

  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

Sources & evidence

ORD record
ord-64de0387def442e2af14790bfd63a406
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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