4-(Tri-n-butylstannyl)pyridine → 4-Chloro-7-fluoro-3-methyl-2-(pyridin-4-yl)quinoline

HRID 1618502Notes

Reaction equation

HRID 1618502 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.C([Sn](CCCC)(CCCC)[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1)CCC>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:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 27373184-(Tri-n-butylstannyl)pyridineHCID 596311082,4-Dichloro-7-fluoro-3-methylquinoline

Product 1

HCID 672847364-Chloro-7-fluoro-3-methyl-2-(pyridin-4-yl)quinoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared according to procedure E using 2,4-dichloro-7-fluoro-3-methylquinoline (500 mg, 2.17 mmol), palladium tetrakistriphenylphosphine (0.251 mg, 0.22 mmol) and 4-tributylstannylpyridine (800 mg, 4.35 mmol) in toluene (15 mL). After purification 4-chloro-7-fluoro-3-methyl-2-(pyridin-4-yl)quinoline was obtained as a white solid.

Workup

  1. customPrepared
  2. customAfter purification 4-chloro-7-fluoro-3-methyl-2-(pyridin-4-yl)quinoline
  3. customwas obtained as a white solid

Sources & evidence

ORD record
ord-7f30bd90b10a49378cffe76f770c04d7
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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