Water → 4-Chloro-6-fluoro-2-(5-fluoropyridin-3-yl)-3-methylquinoline

HRID 1431238Notes

Reaction equation

HRID 1431238 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.[F:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[N:20][CH:21]=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](=[CH:5][CH:6]=[C:7]([F:14])[CH:8]=2)[N:3]=[C:2]([C:18]2[CH:19]=[N:20][CH:21]=[C:16]([F:15])[CH:17]=2)[C:11]=1[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 596312202,4-Dichloro-6-fluoro-3-methylquinoline

Product 1

HCID 596310914-Chloro-6-fluoro-2-(5-fluoropyridin-3-yl)-3-methylquinoline

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to general Procedure F using 2,4-dichloro-6-fluoro-3-methylquinoline (300 mg, 1.3 mmol), 5-fluoropyridin-3-ylboronic acid (160 mg, 1.3 mmol), tetrakis(triphenylphosphine)palladium(0) (151 mg, 0.13 mmol), sodium carbonate (242 mg, 2.28 mmol) in toluene:water (5 mL:2 mL) and heating at 130° C. overnight. After purification 4-chloro-6-fluoro-2-(5-fluoropyridin-3-yl)-3-methylquinoline was obtained as a white solid. Mass Spectrum (ESI) m/e=291.0 (M+1).

Workup

  1. customPrepared
  2. customAfter purification 4-chloro-6-fluoro-2-(5-fluoropyridin-3-yl)-3-methylquinoline
  3. customwas obtained as a white solid

Sources & evidence

ORD record
ord-23801ea3da244b39bc49d77023967b6a
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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