Dimethyl Sulfoxide → 1-(5-Bromo-6-methoxypyridin-2-yl)pyrrolidin-3-ol

HRID 1054877

반응식

HRID 1054877 반응식
[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[NH:11]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12]1.C(N(CC)CC)C.CS(C)=O>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:11]2[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12]2)=[N:4][C:3]=1[O:9][CH3:10]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 982104-HydroxypyrrolidineHCID 532174543-Bromo-6-chloro-2-methoxypyridine

생성물 1

HCID 866988541-(5-Bromo-6-methoxypyridin-2-yl)pyrrolidin-3-ol수율 25.3%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
150 °C

실험 절차

A vial was charged with 3-bromo-6-chloro-2-methoxypyridine (1.00 g, 4.5 mmol), rac-pyrrolidin-3-ol (0.59 g, 6.7 mmol), triethylamine (0.91 g, 8.9 mmol) and dimethylsulfoxide (4 mL). The mixture was heated to 150° C. for 5 hrs. The mixture was cooled to room temperature and diluted with 20 mL of water. The solution was extracted with ethyl acetate (10 mL×3). The extracts were combined, dried (sodium sulfate) and concentrated. The resulting residue was purified through flash column chromatography (petroleum ether/ethyl acetate=5:1˜2:1) to give the title compound (0.26 g, 25.3%) as light brown gum.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe solution was extracted with ethyl acetate (10 mL×3)
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated
  5. customThe resulting residue was purified through flash column chromatography (petroleum ether/ethyl acetate=5:1˜2:1)

출처 및 근거

ORD 기록
ord-7aa9f94236dd4eef849fd646de62ffa9
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394285B2

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