3-(Tributylstannyl)pyridine → HCID 89444365, compound

HRID 593213Notes

Reaction equation

HRID 593213 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:16])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[N:6][CH:7]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Sn](CCCC)(CCCC)CCCC)[CH:18]=1>CN(C)C=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:16]=[C:9]([NH:8][C:5]1[CH:4]=[N:3][C:2]([C:19]2[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=2)=[CH:7][N:6]=1)[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 2

HCID 34838483-(Tributylstannyl)pyridineHCID 89437205HCID 89437205, compound

Product 1

HCID 89444365HCID 89444365, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

Methyl 4-[(5-bromopyrazin-2-yl)amino]-4-oxo-butanoate (A2, 200 mg, 0.694 mmol) was dissolved in N,N-dimethylformamide (4.5 mL) in a microwave vial and 3-pyridyltributylstannane (0.833 mmol, 0.29 mL) and tetrakis(triphenylphosphine) palladium(0) (0.069 mmol) were added. Argon was bubbling through the mixture for ca. 5 min and the vial was heated under microwave irradiations for 10 min at 150° C. The solvent was evaporated and the residue was diluted with acetonitrile, washed with cyclohexane (2×) and evaporated. The product was purified by flash chromatography (RF-machine, AcOEt/cyclohexane: 1/1→1/0) to give methyl 4-oxo-4-[[5-(3-pyridyl)pyrazin-2-yl]amino]butanoate (compound A39) (0.072 g, 36% Yield). LCMS (Method F): RT 0.53 min, 287 (M+H+).

Workup

  1. additionwere added
  2. customArgon was bubbling through the mixture for ca. 5 min
  3. customThe solvent was evaporated
  4. additionthe residue was diluted with acetonitrile
  5. washwashed with cyclohexane (2×)
  6. customevaporated
  7. customThe product was purified by flash chromatography (RF-machine, AcOEt/cyclohexane: 1/1→1/0)

Sources & evidence

ORD record
ord-6c494f0676a84e9d808ec5643867559d
Source dataset
uspto-grants-2016_01
Patent number
US09241489B2

Reaction notes

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