2-(Tributylstannyl)pyridine → 4-Chloro-6-fluoro-3-methyl-2-(pyridin-2-yl)quinoline

HRID 1431241Notes

Reaction equation

HRID 1431241 reaction equation
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([F:14])[CH:8]=2)[N:3]=1.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.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([F:14])[CH:8]=2)[N:3]=[C:2]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[C:11]=1[CH3:12]

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 596312202,4-Dichloro-6-fluoro-3-methylquinoline

Product 1

HCID 596313544-Chloro-6-fluoro-3-methyl-2-(pyridin-2-yl)quinoline

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Prepared according to general Procedure E using 2,4-dichloro-6-fluoro-3-methylquinoline (250 mg, 1.1 mmol), 2-(tributylstannyl)pyridine (400 mg, 1.1 mmol), tetrakis(triphenylphosphine)palladium(0) (63 mg, 0.05 mmol) in toluene (5 mL) and heating at 110° C. overnight. After purification 4-chloro-6-fluoro-3-methyl-2-(pyridin-2-yl)quinoline was obtained as a white solid.

Workup

  1. customPrepared
  2. customAfter purification 4-chloro-6-fluoro-3-methyl-2-(pyridin-2-yl)quinoline
  3. customwas obtained as a white solid

Sources & evidence

ORD record
ord-fdb8c8d0eaf54e13a34875477847d6c2
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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