Trifluoromethanesulfonic anhydride → Trifluoro-methanesulfonic Acid Quinoxalin-5-yl Ester

HRID 751287

Reaction equation

HRID 751287 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[CH:24]=[CH:23][CH:22]=[C:21](O)[C:20]=2[N:19]=[CH:18][CH:17]=1>N1C=CC=CC=1>[N:16]1[C:25]2[C:20](=[C:21]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH:22]=[CH:23][CH:24]=2)[N:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 1356902745-Quinoxalinol

Product 1

HCID 58611956Trifluoro-methanesulfonic Acid Quinoxalin-5-yl EsterYield 85.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Add trifluoromethanesulfonic anhydride (0.66 mL, 3.94 mmol) to a solution of quinoxalin-5-ol (Yamamoto, T. et al., J. Am. Chem. Soc. 1996, 118, 3930-3936; 500 mg, 3.42 mmol) in pyridine (6.8 mL) at 0° C. Allow the reaction to warm slowly to room temperature over 18 h. Add saturated aqueous sodium bicarbonate solution (100 mL) and extract the mixture with methylene chloride (3×100 mL). Dry the combined organic solutions with sodium sulfate, concentrate in vacuo, and purify by flash column chromatography to provide the subtitled compound (810 mg, 85%) as an off-white solid. MS ESI+ m/e 279 (M+1). 1H NMR (CDCl3): δ 8.85 (m, 2H), 8.18 (m, 1H), 7.84 (m, 1H), 7.63 (m, 1H). TLC (SiO2): Rf0.2 (3:1 hexanes/ethyl acetate).

Workup

  1. customthe reaction
  2. extractionAdd saturated aqueous sodium bicarbonate solution (100 mL) and extract the mixture with methylene chloride (3×100 mL)
  3. dry with materialDry the combined organic solutions with sodium sulfate
  4. concentrationconcentrate in vacuo
  5. custompurify by flash column chromatography

Sources & evidence

ORD record
ord-563b5d0e08314816806c971745378742
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Linked notes

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