Triethylamine → Methyl 3-(trifluoromethylsulfonyloxy)-pyridine-2-carboxylate

HRID 1099193Notes

Reaction equation

HRID 1099193 reaction equation
[OH:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[F:19][C:20]([F:26])([F:25])[S:21](Cl)(=[O:23])=[O:22]>ClCCl>[F:19][C:20]([F:26])([F:25])[S:21]([O:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl chlorideHCID 819341Methyl 3-Hydroxy-2-pyridinecarboxylate

Product 1

HCID 11066008Methyl 3-(trifluoromethylsulfonyloxy)-pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 3-hydroxypyridine-2-carboxylate (80 g, 523 mmol) in anhydrous dichloromethane (250 ml) was added triethylamine (58.2 g, 575 mmol). The solution was cooled to 0° C., and trifluoromethanesulfonyl chloride (97 g, 575 mmol) was added dropwise. The reaction suspension was allowed to stir at 0° C. for 1 h, and it was then warmed to rt to stir for 4 h. The solid triethylammonium chloride was removed via filtration, and the filtrate was concentrated in vacuo to yield methyl 3-{[(trifluoromethyl)sulfonyl]oxy}pyridine-2-carboxylate as an oily residue (148.6 g).

Workup

  1. temperatureit was then warmed to rt
  2. stirringto stir for 4 h
  3. customThe solid triethylammonium chloride was removed via filtration
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3a2f780753ea449ab87e710699e4beb4
Source dataset
uspto-grants-2012_03
Patent number
US08143405B2

Reaction notes

Loading…