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2-(Tributylstannyl)pyridine → Methyl 1-methyl-6-oxo-5-(pyridin-2-yl)-1,6-dihydropyridine-3-carboxylate

HRID 253133
Notes
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Reaction equation

HRID 253133 reaction equation
Br[C:2]1[C:7](=[O:8])[N:6]([CH3:9])[CH:5]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)CCC>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:9][N:6]1[C:7](=[O:8])[C:2]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:3][C:4]([C:10]([O:12][CH3:13])=[O:11])=[CH:5]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 59354302Methyl 5-bromo-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 66846039Methyl 1-methyl-6-oxo-5-(pyridin-2-yl)-1,6-dihydropyridine-3-carboxylateYield 39.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst
HCID 962
Water
Solvent
HCID 312751,4-DioxaneSolvent

Procedure

Methyl 5-bromo-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (57 mg, 0.23 mmol), 2-(tributylstannyl)pyridine (85 mg, 0.23 mmol) and tetrakis(triphenylphosphine)palladium (13 mg, 0.012 mmol, Strem) were stirred in 1.5 mL of dioxane at 90° C. for 16 h. The reaction mixture was cooled to RT, diluted with H2O and extracted with EtOAc (2×). The combined organic extracts were washed 1× with brine, dried over MgSO4, filtered and concentrated in vacuo. Purification of the crude residue by column chromatography (4 g pre-packed column, elution 0-30% EtOAc/Hexanes) gave the title compound (22 mg, 39%) as a light yellow solid. MS m/z: 245 (M+1).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed 1× with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the crude residue
  7. washby column chromatography (4 g pre-packed column, elution 0-30% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-a1cf32279e6e4ef5abf20719ad864bce
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07872009B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes