Potassium Bromide → HCID 22034106, compound

HRID 1813925Notes

Reaction equation

HRID 1813925 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10](OS(C(F)(F)F)(=O)=O)[C:9]2[C:4](=[C:5]([C:20]3[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=3[CH3:28])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Br-:29].[K+]>CS(C)=O.C1COCC1>[Br:29][C:10]1[C:9]2[C:4](=[C:5]([C:20]3[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=3[CH3:28])[CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([CH3:1])[CH:11]=1

Participants

5

Reactant 2

HCID 253877Potassium BromideHCID 54320035HCID 54320035, compound

Product 1

HCID 22034106HCID 22034106, compoundYield 105.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of trifluoro-methanesulfonic acid 2-methyl-8-(2,4,6-trimethyl-phenyl)-quinolin-4-yl ester (426 mg, 1 mmol) and potassium bromide (KBr) (809 mg, 1.1 mmol) in a mixture of 1 ml of dry DMSO and 3 ml of dry THF was heated in 120° C. oil bath for 3 hours. The mixture was quenched with water, extracted with ethyl acetate. The organic layer was dried and concentrated to give 358 mg of the title compound as an off-white solid. 1H NMR (CDCl3) δ 8.16 (m,1H), 7.59 (m,1H), 7.56(s,1H), 7.48(m,1H), 6.97(s,1H), 2.53(s,3H), 2.37(s,3H), 1.87(,6H) ppm.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-700c5712e9134bbd859af4436c10d433
Source dataset
uspto-grants-2005_04
Patent number
US06875769B2

Reaction notes

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