Potassium peroxymonosulphate → 5-Chloro-6-cyclopropylpyridin-3-OL

HRID 512063노트

반응식

HRID 512063 반응식
[Cl:1][C:2]1[C:3]([CH:17]2[CH2:19][CH2:18]2)=[N:4][CH:5]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:7]=1.S([O-])(O[O-])(=O)=[O:21].[K+].[K+]>CC(C)=O.O.CC(OC)(C)C>[Cl:1][C:2]1[CH:7]=[C:6]([OH:21])[CH:5]=[N:4][C:3]=1[CH:17]1[CH2:19][CH2:18]1

참가 물질

6

반응물 2

HCID 10313463Potassium peroxymonosulphateHCID 58042381(5-Chloro-6-cyclopropylpyridin-3-yl)boronic acid pinacol ester

생성물 1

HCID 580424875-Chloro-6-cyclopropylpyridin-3-OL수율 42%

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 15413tert-Butyl methyl ether용매

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온도
0 °C

실험 절차

3-Chloro-2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (Preparation 41, 3.092 mmol assuming 100% in previous step) was dissolved in acetone (10.0 mL) and cooled to 0° C. with an ice bath. Then potassium peroxymonosulfate (2.55 g, 4.15 mmol) in water (10.0 mL) was added dropwise to the mixture and stirred at this temperature for 1 hour. The reaction was then diluted in TBME (25.0 mL) and washed with brine (3×25.0 mL). The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified with silica gel chromatography eluting with 0 to 30% EtOAc in heptane to yield the title compound as a pale yellow solid (0.220 g, 1.28 mmol, 42% over 2 steps).

후처리

  1. washwashed with brine (3×25.0 mL)
  2. dry with materialThe organic layer was then dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting crude product was purified with silica gel chromatography
  6. washeluting with 0 to 30% EtOAc in heptane

출처 및 근거

ORD 기록
ord-a34fcdbbf675419da01a0c5b5b82f83c
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102621B2

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