Pyridine → Quinolin-7-yl trifluoromethanesulfonate

HRID 709243Notes

Reaction equation

HRID 709243 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[N:16]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23](O)[CH:24]=2)[CH:19]=[CH:18][CH:17]=1.N1C=CC=CC=1>ClCCl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:23]1[CH:24]=[C:25]2[C:20]([CH:19]=[CH:18][CH:17]=[N:16]2)=[CH:21][CH:22]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 1354268667-Hydroxyquinoline

Product 1

HCID 59296115Quinolin-7-yl trifluoromethanesulfonateYield 86.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (1.40 mL, 8.32 mmol) was added dropwise via a syringe to a solution of quinolin-7-ol (930 mg, 6.41 mmol), and pyridine (1.05 mL, 13.0 mmol) in anhydrous dichloromethane (50 mL) at 0° C. After addition the ice bath was removed and the reaction was allowed to warm to room temperature and stirred overnight. The reaction was concentrated and purified via flash chromatography using an Analogix SF25-40 g column and eluant of ethyl acetate in heptane (0-40%) to afford the title compound as an orange-white solid (1.54 g, 86.7%). LC-MS m/z 278.4 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.42-7.57 (m, 2H) 7.95 (d, J=8.98 Hz, 1H) 8.05 (d, J=2.54 Hz, 1H) 8.20-8.29 (m, 1H) 8.97-9.06 (m, 1H).

Workup

  1. customwas removed
  2. concentrationThe reaction was concentrated
  3. custompurified via flash chromatography

Sources & evidence

ORD record
ord-059afba43de1425d95e7847bbe1b6656
Source dataset
uspto-grants-2015_11
Patent number
US09180123B2

Reaction notes

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