2-(Tributylstannyl)-1,3-thiazole → 2-(4-Chloro-8-fluoro-3-methylquinolin-2-yl)thiazole

HRID 1431228Notes

Reaction equation

HRID 1431228 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.C([Sn](CCCC)(CCCC)[C:20]1[S:21][CH:22]=[CH:23][N:24]=1)CCC>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:20]2[S:21][CH:22]=[CH:23][N:24]=2)[C:11]=1[CH3:12]

Participants

5

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 596310312,4-Dichloro-8-fluoro-3-methylquinoline

Product 1

HCID 596311892-(4-Chloro-8-fluoro-3-methylquinolin-2-yl)thiazole

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to Procedure E using 2,4-dichloro-8-fluoro-3-methylquinoline (250 mg, 1.087 mmol), 2-tributylstannylthiazole (0.34 mL, 1.087 mmol) and tetrakis(triphenylphosphine)palladium(0) (126 mg, 0.109 mmol) in toluene (4 mL) and heating at reflux overnight. After purification 2-(4-chloro-8-fluoro-3-methylquinolin-2-yl)thiazole was obtained.

Workup

  1. customPrepared
  2. temperatureheating
  3. temperatureat reflux overnight
  4. customAfter purification 2-(4-chloro-8-fluoro-3-methylquinolin-2-yl)thiazole
  5. customwas obtained

Sources & evidence

ORD record
ord-19d92524b5a84939b0e34cfac4243f28
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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