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

HRID 1431482Notes

Reaction equation

HRID 1431482 reaction equation
Cl[C:2]1[C:11]([CH:12]([CH3:14])[CH3:13])=[C:10]([Cl:15])[C:9]2[C:4](=[CH:5][C:6]([F:16])=[CH:7][CH:8]=2)[N:3]=1.[CH3:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20]([Sn](CCCC)(CCCC)CCCC)[CH:19]=1>C1(C)C=CC=CC=1>[Cl:15][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:16])=[CH:7][CH:8]=2)[N:3]=[C:2]([C:20]2[CH:19]=[C:18]([CH3:17])[CH:23]=[CH:22][N:21]=2)[C:11]=1[CH:12]([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 112227754-Methyl-2-(tributylstannyl)pyridineHCID 596311212,4-Dichloro-7-fluoro-3-isopropylquinoline

Product 1

HCID 596313654-Chloro-7-fluoro-3-isopropyl-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-isopropylquinoline (0.3 g, 1.162 mmol), 4-methyl-2-(tributylstannyl)pyridine (0.489 g, 1.28 mmol) and palladium tetrakistriphenylphosphine (0.134 g, 0.12 mmol) in toluene (2.3 mL) at 100° C. for 6.5 days to give 4-chloro-7-fluoro-3-isopropyl-2-(4-methylpyridin-2-yl)quinoline as a white solid. Mass Spectrum (ESI) m/e=315.1 (M+1).

Workup

  1. customwas prepared
  2. customat 100° C.
  3. customfor 6.5 days

Sources & evidence

ORD record
ord-39a89644438c49f3aa80ca9149de65e4
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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