Potassium Carbonate → 6-(Methylsulfonyl)pyridin-3-ol

HRID 518404

반응식

HRID 518404 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][S:10]([O:12][Na])=[O:11].N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I.O>[CH3:9][S:10]([C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1)(=[O:12])=[O:11]

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 8198212-Chloro-5-hydroxypyridineHCID 178504973HCID 178504973, 화합물

생성물 1

HCID 231451966-(Methylsulfonyl)pyridin-3-ol수율 44.9%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
140 °C

실험 절차

A mixture of 6-chloropyridin-3-ol (2.00 g, 15.44 mmol), MeSO2Na (2.36 g, 23.16 mmol), CuI (882.16 mg, 4.63 mmol), L-proline (533.28 mg, 4.63 mmol), and K2CO3 (640.19 mg, 4.63 mmol) in DMSO (20 mL) were charged into a microwave tube. The sealed tube was heated at 140° C. for 3 hrs under microwave. After cooling to room temperature, water (100 mL) was added. The mixture was extracted with EtOAc (100 mL×3). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to give the title compound (1.2 g, 44.8%) as a yellow solid. 1H NMR (Methanol-d4, 400 MHz) δ 8.24 (d, J=2.4 Hz, 1H), 7.94 (d, J=8.4 Hz, 1H), 7.37 (dd, J1=8.8 Hz, J2=2.8 Hz, 1H), 3.15 (s, 3H).

후처리

  1. additionwere charged into a microwave tube
  2. temperatureAfter cooling to room temperature
  3. extractionThe mixture was extracted with EtOAc (100 mL×3)
  4. washThe combined organic layers were washed with brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-11b931590f4240538a587e6d7b16418c
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115114B2

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