2-(Tributylstannyl)pyrazine → HCID 86701167, compound

HRID 572125Notes

Reaction equation

HRID 572125 reaction equation
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([Cl:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([Sn](CCCC)(CCCC)[C:20]1[CH:25]=[N:24][CH:23]=[CH:22][N:21]=1)CCC>O1CCOCC1.[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>[Cl:14][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([C:20]1[CH:25]=[N:24][CH:23]=[CH:22][N:21]=1)[C:11]([CH:12]=[O:13])=[CH:10]2

Participants

5

Reactant 2

HCID 27373162-(Tributylstannyl)pyrazineHCID 149171252,8-Dichloro-quinoline-3-carbaldehyde

Product 1

HCID 86701167HCID 86701167, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2,8-dichloroquinoline-3-carbaldehyde (2.3 g, 10.18 mmol), 2-(tributylstannanyl)pyrazine (4.5 g, 12.2 mmol) and tetrakis(triphenylphosphine)-palladium(0) (0.4 g, 0.35 mmol) in 1,4-dioxane (25 mL) was degassed and the mixture was heated under nitrogen at 110° C. for 5 h. The mixture was allowed to cool to room temperature overnight and the solidified product was collected by filtration and washed repeatedly with ether. The filtrate was concentrated and left in a refrigerator for 2 h to give a second crop, which was filtered, washed with ether and combined with the bulk material to give the title compound (2.74 g, 99%) as a yellow crystalline solid. LCMS (ES+) 270 (M+H)+, RT 1.41 minutes.

Workup

  1. customwas degassed
  2. temperatureto cool to room temperature overnight
  3. filtrationthe solidified product was collected by filtration
  4. washwashed repeatedly with ether
  5. concentrationThe filtrate was concentrated
  6. customto give a second crop, which
  7. filtrationwas filtered
  8. washwashed with ether

Sources & evidence

ORD record
ord-e18c4a149b8143c1bdcf596a05129f05
Source dataset
uspto-grants-2015_05
Patent number
US09029392B2

Reaction notes

Loading…