Dimethylformamide → HCID 67380693, compound

HRID 1422836Notes

Reaction equation

HRID 1422836 reaction equation
CN(C)C=O.[CH3:6][O:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([SH:15])[CH:10]=1.CC(C)([O-])C.[K+].Br[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][N:25]=1>O>[CH3:6][O:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([S:15][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][N:25]=2)[CH:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8170982-Bromo-5-chloropyridineHCID 4362804Methyl 3-mercaptobenzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 67380693HCID 67380693, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dimethylformamide (7.0 mL) solution of 3-mercapto-benzoic acid methyl ester (600 mg, 3.5 mmol) was added potassium t-butoxide (500 mg, 4.0 mmol). Upon stirring the reaction at room temperature for 15 min, 2-bromo-5-chloro-pyridine (700 mg, 3.5 mmol) was added. The reaction was stirred at room temperature for 15 h. Crude reaction mass was added to water, aqueous layer was acidified to pH 4.0 and product was extracted with ethyl acetate to give 3-(5-chloro-pyridin-2-ylsulfanyl)-benzoic acid methyl ester (780 mg).

Workup

  1. customthe reaction at room temperature for 15 min
  2. stirringThe reaction was stirred at room temperature for 15 h
  3. customCrude reaction mass
  4. extractionwas extracted with ethyl acetate

Sources & evidence

ORD record
ord-b8ce115bea6f480185a89320c0cf8e1a
Source dataset
uspto-grants-2015_01
Patent number
US08927549B2

Reaction notes

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