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

HRID 518404

反応式

HRID 518404 の反応式
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]

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 8198212-Chloro-5-hydroxypyridineHCID 178504973HCID 178504973、化合物

生成物 1

HCID 231451966-(Methylsulfonyl)pyridin-3-ol収率 44.9%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
140 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-11b931590f4240538a587e6d7b16418c
出典データセット
uspto-grants-2015_08
特許番号
US09115114B2

関連ノート

読み込み中…