2-(Tributylstannyl)pyridine → HCID 59631221, compound

HRID 1431396Notes

Reaction equation

HRID 1431396 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](Cl)[C:8]([CH3:13])=[C:7]2[Cl:14].C([Sn](CCCC)(CCCC)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)CCC>C1(C)C=CC=CC=1>[Cl:14][C:7]1[C:6]2[C:11](=[C:2]([C:9]3[CH:8]=[CH:7][CH:6]=[CH:11][N:10]=3)[CH:3]=[CH:4][CH:5]=2)[N:10]=[C:9]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:20][N:21]=2)[C:8]=1[CH3:13]

Participants

4

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 59631271HCID 59631271, compound

Product 1

HCID 59631221HCID 59631221, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 8-bromo-2,4-dichloro-3-methylquinoline (0.35 g, 1.21 mmol) in toluene (2.4 mL) was added 2-(tributylstannyl)pyridine (0.94 mL, 2.55 mmol), and palladium tetrakistriphenylphosphine (0.140 g, 0.12 mmol). The reaction was stirred at 100° C. and stirring continued for 19 h. After which the reaction mixture was cooled to rt and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (0 to 50% EtOAc in hexane) to give the desired product 4-chloro-3-methyl-2,8-di(pyridin-2-yl)quinoline as a white solid. Mass Spectrum (ESI) m/e=332.0 (M+1).

Workup

  1. stirringstirring
  2. temperatureAfter which the reaction mixture was cooled to rt
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography on silica gel (0 to 50% EtOAc in hexane)

Sources & evidence

ORD record
ord-0ebcb03005b445b3ba2809e78e97de86
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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