4-Methyl-2-(tributylstannyl)pyridine → 4,8-Dichloro-3-methyl-2-(4-methylpyridin-2-yl)quinoline

HRID 1431535Notes

Reaction equation

HRID 1431535 reaction equation
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[C:5]([Cl:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([Sn](CCCC)(CCCC)CCCC)[CH:17]=1>C1(C)C=CC=CC=1>[Cl:13][C:10]1[C:9]2[C:4](=[C:5]([Cl:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([C:18]2[CH:17]=[C:16]([CH3:15])[CH:21]=[CH:20][N:19]=2)[C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 112227754-Methyl-2-(tributylstannyl)pyridineHCID 596312172,4,8-Trichloro-3-methylquinoline

Product 1

HCID 596311454,8-Dichloro-3-methyl-2-(4-methylpyridin-2-yl)quinoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The Stille coupled product was prepared according to Procedure E using 2,4,8-trichloro-3-methylquinoline (0.15 g, 0.61 mmol), 4-methyl-2-(tributylstannyl)-pyridine (0.26 g, 0.67 mmol), palladium tetrakistriphenylphosphine (0.070 g, 0.06 mmol) in toluene (1.2 mL) to give 4,8-dichloro-3-methyl-2-(4-methylpyridin-2-yl)quinoline as a light yellow solid. Mass Spectrum (ESI) m/e=303.0 (M+1).

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-89f1b9ca576c4a0aacb2a882151f6414
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

Loading…