Water → 3-(4-Chloro-7-fluoro-3-methylquinolin-2-yl)benzonitrile

HRID 1618493Notes

Reaction equation

HRID 1618493 reaction equation
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=1.[C:15]([C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)#[N:16].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][C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=[C:2]([C:21]2[CH:22]=[C:17]([CH:18]=[CH:19][CH:20]=2)[C:15]#[N:16])[C:11]=1[CH3:12]

Participants

6

Reactant 3

HCID 962WaterHCID 27343253-Cyanophenylboronic acidHCID 596311082,4-Dichloro-7-fluoro-3-methylquinoline

Product 1

HCID 672855433-(4-Chloro-7-fluoro-3-methylquinolin-2-yl)benzonitrile

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to procedure F using 2,4-dichloro-7-fluoro-3-methylquinoline (500 mg, 2.17 mmol), 3-cyanophenylboronic acid (319 mg, 2.17 mmol), Pd(PPh3)4 (251 mg, 0.22 mmol) in toluene:water (10 mL:4 mL) and heating at reflux overnight. After purification, 3-(4-chloro-7-fluoro-3-methylquinolin-2-yl)benzonitrile was obtained as a white solid.

Workup

  1. customPrepared
  2. temperatureat reflux overnight
  3. customAfter purification

Sources & evidence

ORD record
ord-4709cb7fb0804fe599b700f1a1fcc785
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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