Water → 4-Chloro-8-fluoro-3-methyl-2-(pyridin-3-yl)quinoline

HRID 1431240Notes

Reaction equation

HRID 1431240 reaction equation
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[C:5]([F:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17](B(O)O)[CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].O>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](=[C:5]([F:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([C:17]2[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=2)[C:11]=1[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 596310312,4-Dichloro-8-fluoro-3-methylquinoline

Product 1

HCID 596313004-Chloro-8-fluoro-3-methyl-2-(pyridin-3-yl)quinoline

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to general Procedure F using 2,4-dichloro-8-fluoro-3-methylquinoline (250 mg, 1.1 mmol), 3-pyridylboronic acid (134 mg, 1.1 mmol), tetrakis(triphenylphosphine)palladium(0) (126 mg, 0.11 mmol), sodium carbonate (202 mg, 1.90 mmol) in toluene:water (5 mL:2 mL) and heating at 130° C. overnight. After purification 4-chloro-8-fluoro-3-methyl-2-(pyridin-3-yl)quinoline was obtained as a white solid. Mass Spectrum (ESI) m/e=273.0 (M+1).

Workup

  1. customPrepared
  2. customAfter purification 4-chloro-8-fluoro-3-methyl-2-(pyridin-3-yl)quinoline
  3. customwas obtained as a white solid

Sources & evidence

ORD record
ord-01775db38e614664bfeab8c5234e4e75
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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