Trifluoromethanesulfonic anhydride → Methyl 3-(trifluoromethylsulfonyloxy)-pyridine-2-carboxylate

HRID 625549노트

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HRID 625549 반응식
[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[C:18]([C:23]([O:25][CH3:26])=[O:24])=[N:19][CH:20]=[CH:21][CH:22]=1>C(Cl)Cl>[F:5][C:4]([F:7])([F:6])[S:1]([O:8][C:17]1[C:18]([C:23]([O:25][CH3:26])=[O:24])=[N:19][CH:20]=[CH:21][CH:22]=1)(=[O:3])=[O:2]

참가 물질

4

반응물 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 819341Methyl 3-Hydroxy-2-pyridinecarboxylate

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

Triflic anhydride (5.0 g, 18.0 mmol) was added dropwise to a cold (0° C.) solution of methyl 3-hydroxypicolinate (2.5 g, 16.3 mmol) and TEA (2.5 mL, 18.0 mmol) in CH2Cl2 (80 mL). The mixture was stirred at 0° C. for 1 h before it was allowed to warm up to room temperature where it stirred for an additional 1 h. The mixture was then quenched with saturated NaHCO3 solution (40 mL) and the organic layer was separated, washed with brine, dried over MgSO4 and concentrated to give methyl 3-(trifluoromethylsulfonyloxy)picolinate (i.e., Cap-174, step a) (3.38 g, 73%) as a dark brown oil (>95% pure) which was used directly without further purification. 1H NMR (300 MHz, CDCl3) δ ppm 8.72-8.79 (1H, m), 7.71 (1H, d, J=1.5 Hz), 7.58-7.65 (1H, m), 4.04 (3H, s). Rt=1.93 min (Cond.-MD1); LC-MS: Anal. Calcd. for [M+H]+ C8H7F3NO5S: 286.00. found: 286.08.

후처리

  1. temperatureto warm up to room temperature where it
  2. stirringstirred for an additional 1 h
  3. customThe mixture was then quenched with saturated NaHCO3 solution (40 mL)
  4. customthe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a7de72a5e4da4f659f2b1782554516df
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303007B2

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