2-(Tributylstannyl)pyridine → HCID 59631221, compound

HRID 1431334Notes

Reaction equation

HRID 1431334 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

Procedure

The chlorides were prepared according to Procedure E using 8-bromo-2,4-dichloro-3-methylquinoline (0.32 g, 1.11 mmol), 2-(tributylstannyl)pyridine (0.45 mL, 1.23 mmol) and palladium tetrakistriphenylphosphine (0.13 g, 0.11 mmol) in toluene (2.2 mL) to give 8-bromo-4-chloro-3-methyl-2-(pyridin-2-yl)quinoline and further elution gave 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. customto give
  2. wash8-bromo-4-chloro-3-methyl-2-(pyridin-2-yl)quinoline and further elution

Sources & evidence

ORD record
ord-48e2a118de9c4b01b05f50f5d8851da1
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

Loading…