Pyridine → 6-Quinolinyl trifluoromethanesulfonate

HRID 1930332Notes

Reaction equation

HRID 1930332 reaction equation
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].O[C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][CH:21]=[CH:20]2.N1C=CC=CC=1>C(Cl)Cl>[F:5][C:4]([F:7])([F:6])[S:1]([O:8][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][CH:21]=[CH:20]2)(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 113746-HydroxyquinolineHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 152903586-Quinolinyl trifluoromethanesulfonateYield 104.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triflic anhydride (42.8 g, 0.15 mol) in methylene chloride (100 mL) was added dropwise to a 0° C. solution of 6-hydroxyquinoline (20.00 g, 0.138 mol) and pyridine (23 g, 0.277 mol) in methylene chloride (500 mL). The cooling bath was removed and the resulting solution was stirred at RT for 4 h. The reaction mixture was washed with water (3×300 mL) and the organics were dried (MgSO4) and concentrated under vacuum to afford crude quinolin-6-yl trifluoromethanesulfonate (40 g, >100% yield) as an oil. 1H-NMR (400 MHz, DMSO-d6): δ 9.00 (d, 1 H, J=2.8 Hz), 8.50 (d, 1H, J=8.0 Hz), 8.21 (d, J=2.8 Hz, 1H), 8.18 (d, J=9.2 Hz, 1H), 7.80 (m, 1 H), 7.64 (m, 1 H); MS (ESI) m/z: 277.9 (M+H+).

Workup

  1. customThe cooling bath was removed
  2. washThe reaction mixture was washed with water (3×300 mL)
  3. dry with materialthe organics were dried (MgSO4)
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a4dd279842bc4f0d87f1bc65e5fb611e
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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