Trifluoromethanesulfonic acid → 6-Trifluoromethylsulfonyloxy-8-methoxy-1,7-naphthyridine

HRID 369034

Reaction equation

HRID 369034 reaction equation
N[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH3:13])[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[F:14][C:15]([F:21])([F:20])[S:16]([OH:19])(=[O:18])=[O:17].N([O-])=O.[Na+]>O>[F:14][C:15]([F:21])([F:20])[S:16]([O:19][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH3:13])[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 46725998-Methoxy-1,7-naphthyridin-6-amineHCID 23668193Sodium Nitrite

Product 1

HCID 232846356-Trifluoromethylsulfonyloxy-8-methoxy-1,7-naphthyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 6-amino-8-methoxy-1,7-naphthyridine (19 g, 0.108 mol) in a 1:1 mixture of water and trifluoromethane sulfonic acid (380 ml) is carefully added a solution of sodium nitrite (11.2 g, 0.162 mol) in water (40 ml) at 0° C. After 1 h the cooling bath is removed and the reaction mixture stirred for an other hour at ambient temperature. Then, ethyl acetate (500 ml) is added and the solution is neutralized by adding sodium bicarbonate (4N, 1 l). The water phase is extracted again with ethyl acetate (3×500 ml). The organic solvent is evaporated and the crude product is purified by flash column chromatography on silica gel (20:3 toluene/acetone) affording the title compound. M+308; Melting point 99-101° C.

Workup

  1. customAfter 1 h the cooling bath is removed
  2. additionThen, ethyl acetate (500 ml) is added
  3. additionby adding sodium bicarbonate (4N, 1 l)
  4. extractionThe water phase is extracted again with ethyl acetate (3×500 ml)
  5. customThe organic solvent is evaporated
  6. customthe crude product is purified by flash column chromatography on silica gel (20:3 toluene/acetone)

Sources & evidence

ORD record
ord-0752721364024996b548b4ef802fbc9c
Source dataset
uspto-grants-2000_10
Patent number
US06136821

Linked notes

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