2-(Tributylstannyl)pyridine → HCID 59631359, compound

HRID 1431326Notes

Reaction equation

HRID 1431326 reaction equation
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:15])=[C:7]([Cl:14])[CH:8]=2)[N:3]=1.Cl[C:17]1[C:26](C)=[C:25](Cl)[C:24]2[C:19](=CC=C(Cl)C=2F)[N:18]=1.C([Sn](CCCC)(CCCC)C1C=CC=CN=1)CCC>C1(C)C=CC=CC=1>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:15])=[C:7]([Cl:14])[CH:8]=2)[N:3]=[C:2]([C:17]2[CH:26]=[CH:25][CH:24]=[CH:19][N:18]=2)[C:11]=1[CH3:12]

Participants

5

Reactant 3

HCID 6077842-(Tributylstannyl)pyridineHCID 59631053HCID 59631053, compoundHCID 59631435HCID 59631435, compound

Product 1

HCID 59631359HCID 59631359, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The stille coupled products were prepared according to Procedure E using a mixture of 2,4,6-trichloro-7-fluoro-3-methylquinoline and 2,4,6-trichloro-5-fluoro-3-methylquinoline (0.50 g, 1.90 mmol), 2-(tributylstannyl)pyridine (0.77 mL, 2.08 mmol), palladium tetrakistriphenylphosphine (0.22 g, 0.19 mmol) in toluene (1.90 mL) to give 4,6-dichloro-7-fluoro-3-methyl-2-(pyridin-2-yl)-quinoline as a white solid. Further elution gave 4,6-dichloro-5-fluoro-3-methyl-2-(pyridin-2-yl)quinoline as a white solid. Mass Spectrum (ESI) m/e=307.0 (M+1). Further elution gave 4-chloro-7-fluoro-3-methyl-2,6-di(pyridin-2-yl)-quinoline.

Workup

  1. customwere prepared

Sources & evidence

ORD record
ord-6998cf56fcd94b9a911548c1b003ddca
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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