Sodium hydride → 5-Bromo-2-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-pyridine

HRID 332334노트

반응식

HRID 332334 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][OH:14])=[C:11]([CH3:15])[O:10][N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:19]1[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][N:20]=1>C1COCC1.CO.O>[Br:25][C:22]1[CH:23]=[CH:24][C:19]([O:14][CH2:13][C:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[N:9][O:10][C:11]=2[CH3:15])=[N:20][CH:21]=1

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 27344145-Bromo-2-chloropyridineHCID 28473136(3-(4-Fluorophenyl)-5-methylisoxazol-4-yl)methanol

생성물 1

HCID 684428165-Bromo-2-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-pyridine수율 15%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a a solution of [3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-methanol (500 mg, 2.41 mmol) in THF (5 mL) at room temperature was added sodium hydride (55% dispersion in mineral oil, 137 mg, 3.1 mmol) and the reaction mixture stirred at room temperature for 1 h. Then a solution of 2-chloro-5-bromo-pyridine (484 mg, 2.41 mmol) in THF (5 mL) was added at room temperature and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was then diluted with methanol and water and the mixture was extracted with ethyl acetate. The combined organic layers were then washed with water and brine and then dried over sodium sulfate, filtered and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=9:1 to 4:1) afforded the title compound (128 mg, 15%) which was obtained as a colourless oil. MS: m/e=363.1/365.1 [M+H]+.

후처리

  1. stirringthe reaction mixture was stirred at room temperature for 2 h
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layers were then washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by chromatography (SiO2, heptane:ethyl acetate=9:1 to 4:1)

출처 및 근거

ORD 기록
ord-6bf53bc9e5fd4c1b87d9763b3bf51085
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877783B2

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