2,8-Dichloro-quinoline-3-carbaldehyde → 8-Chloro-2-(6-methoxypyrazin-2-yl)quinoline-3-carbaldehyde

HRID 572126Notes

Reaction equation

HRID 572126 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.[CH3:15][O:16][C:17]1[CH:22]=[N:21][CH:20]=[C:19]([Sn](CCCC)(CCCC)CCCC)[N:18]=1>O1CCOCC1>[Cl:14][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([C:19]1[CH:20]=[N:21][CH:22]=[C:17]([O:16][CH3:15])[N:18]=1)[C:11]([CH:12]=[O:13])=[CH:10]2

Participants

4

Reactant 2

HCID 149171252,8-Dichloro-quinoline-3-carbaldehydeHCID 164271032-Methoxy-6-(tributylstannyl)pyrazine

Product 1

HCID 867011688-Chloro-2-(6-methoxypyrazin-2-yl)quinoline-3-carbaldehydeYield 63.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2,8-dichloroquinoline-3-carbaldehyde (0.5 g, 2.21 mmol), 2-methoxy-6-(tributylstannanyl)pyrazine (1.0 g, 2.51 mmol) and tetrakis(triphenyl-phosphine)palladium(0) (0.2 g, 0.173 mmol) in 1,4-dioxane (10 mL) was degassed and heated at 110° C. overnight. The mixture was allowed to cool to room temperature and diluted with EtOAc. The resulting solid was collected by filtration, washed with EtOAc, then ether, and dried to give the title compound (0.42 g, 63%) as a yellow solid. δH(DMSO-d6) 10.58 (s, 1H), 9.24 (s, 1H), 8.93 (s, 1H), 8.53 (s, 1H), 8.27 (dd, J 8.3, 1.2 Hz, 1H), 8.17 (dd, J 7.5, 1.2 Hz, 1H), 7.75 (m, 1H), 3.96 (s, 3H). LCMS (ES+) 300 (M+H)+, RT 1.51 minutes.

Workup

  1. customwas degassed
  2. temperatureto cool to room temperature
  3. additiondiluted with EtOAc
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with EtOAc
  6. dry with materialether, and dried

Sources & evidence

ORD record
ord-3e2e90a550e94e229125eb32bf4e785c
Source dataset
uspto-grants-2015_05
Patent number
US09029392B2

Reaction notes

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