Dimethylformamide → 5-Fluoro-2-[(1-methyl-1H-pyrazol-5-yl)methoxy]pyridine

HRID 238393

반응식

HRID 238393 반응식
[H-].[Na+].CN(C)C=O.[CH3:8][N:9]1[C:13]([CH2:14][OH:15])=[CH:12][CH:11]=[N:10]1.F[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][N:18]=1>O>[F:23][C:20]1[CH:21]=[CH:22][C:17]([O:15][CH2:14][C:13]2[N:9]([CH3:8])[N:10]=[CH:11][CH:12]=2)=[N:18][CH:19]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27628712,5-DifluoropyridineHCID 11815316(1-methyl-1H-pyrazol-5-yl)methanol

생성물 1

HCID 866848895-Fluoro-2-[(1-methyl-1H-pyrazol-5-yl)methoxy]pyridine수율 58.4%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

60% Sodium hydride (390 mg) was added to a dimethylformamide (9.0 mL) solution of (1-methyl-1H-pyrazol-5-yl)methanol (1.00 g) at a room temperature, and the obtained solution was then stirred for 2 hours. Thereafter, 2,5-difluoropyridine (1.17 g) was added to the reaction solution, and the mixed solution was then stirred for 16 hours. Subsequently, water was added to the reaction solution, and the obtained mixture was then extracted with hexane/ethyl acetate (1/2). The organic layer was concentrated under a reduced pressure. The residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=95:5 to 60:40), so as to obtain the title compound (1.08 g) in the form of a colorless solid.

후처리

  1. stirringthe mixed solution was then stirred for 16 hours
  2. extractionthe obtained mixture was then extracted with hexane/ethyl acetate (1/2)
  3. concentrationThe organic layer was concentrated under a reduced pressure
  4. customThe residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=95:5 to 60:40)

출처 및 근거

ORD 기록
ord-c45fde6b78664f38bfbe9e95d356dfa5
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642626B2

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