4-Methyl-2-(tributylstannyl)pyridine → 4-Chloro-7-fluoro-3-methyl-2-(4-methylpyridin-2-yl)quinoline

HRID 1431484Notes

Reaction equation

HRID 1431484 reaction equation
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:14])=[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](=[CH:5][C:6]([F:14])=[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 596311082,4-Dichloro-7-fluoro-3-methylquinoline

Product 1

HCID 596310864-Chloro-7-fluoro-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-dichloro-7-fluoro-3-methylquinoline (0.109 g, 0.47 mmol), 4-methyl-2-(tributylstannyl)pyridine (0.199 g, 0.52 mmol), palladium tetrakistriphenylphosphine (0.055 g, 0.047 mmol) in toluene (2 mL) to give 4-chloro-7-fluoro-3-methyl-2-(4-methylpyridin-2-yl)quinoline as a white solid. Mass Spectrum (ESI) m/e=287.0 (M+1).

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-5eb2399724ce442e812119805417b4a2
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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