Methanesulfonyl chloride → Methyl 6-(1-(methylsulfonyloxy)ethyl)nicotinate

HRID 1427468Notes

Reaction equation

HRID 1427468 reaction equation
[OH:1][CH:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=1)[CH3:3].[CH3:14][S:15](Cl)(=[O:17])=[O:16]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:14][S:15]([O:1][CH:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=1)[CH3:3])(=[O:17])=[O:16]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 66803327Methyl 6-(1-hydroxyethyl)nicotinate

Product 1

HCID 88541636Methyl 6-(1-(methylsulfonyloxy)ethyl)nicotinateYield 93.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of methyl 6-(1-hydroxyethyl)nicotinate (0.100 g, 0.552 mmol) and 4-dimethylaminopyridine (152 mg, 1.32 mmol) in dichloromethane (10 mL) was added methanesulfonyl chloride (75.9 mg, 0.662 mmol) dropwise. The resulting mixture was stirred at room temperature for 1 hour. Additional methanesulfonyl chloride (75.9 mg, 0.662 mmol) was added and the mixture stirred at room temperature for an additional 2 hours. The mixture was quenched with water and extracted with dichloromethane. The organic layer was dried over sodium sulfate, filtered and concentrated to give crude methyl 6-(1-(methylsulfonyloxy)ethyl)nicotinate (134 mg) as an oil which was used in the next step directly.

Workup

  1. stirringthe mixture stirred at room temperature for an additional 2 hours
  2. customThe mixture was quenched with water
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-814f4210a4374213b8fea137bcecfeb1
Source dataset
uspto-grants-2015_01
Patent number
US08933104B2

Reaction notes

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