Ammonium Chloride → 1-(1-Methyl-1H-pyrazol-5-yl)-3-[4-(trifluoromethyl)phenyl]prop-2-yn-1-one

HRID 238377

반응식

HRID 238377 반응식
C[Mg]Br.[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)#[CH:5].CON(C)[C:19]([C:21]1[N:25]([CH3:26])[N:24]=[CH:23][CH:22]=1)=[O:20].[Cl-].[NH4+]>O1CCCC1>[CH3:26][N:25]1[C:21]([C:19](=[O:20])[C:5]#[C:4][C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:13])([F:14])[F:15])=[CH:8][CH:7]=2)=[CH:22][CH:23]=[N:24]1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 43482951-Ethynyl-4-(trifluoromethyl)benzeneHCID 62038410N-methoxy-N,1-dimethyl-1H-pyrazole-5-carboxamideHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 866848751-(1-Methyl-1H-pyrazol-5-yl)-3-[4-(trifluoromethyl)phenyl]prop-2-yn-1-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

Methyl magnesium bromide (9.70 mL, 1.0 M tetrahydrofuran solution) was added dropwise to a tetrahydrofuran (4.0 mL) solution of 1-ethynyl-4-(trifluoromethyl)benzene (1.80 mL) under cooling in an ice bath, and the obtained solution was then stirred for 2 hours. Thereafter, the reaction solution was cooled to −78° C., and a tetrahydrofuran (6.2 mL) solution of N-methoxy-N,1-dimethyl-1H-pyrazol-5-carboxamide (867 mg) was then added thereto. The obtained mixture was stirred for 1 hour, and was then stirred for 2.5 hours under cooling in an ice bath. Thereafter, a saturated ammonium chloride aqueous solution was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was washed with a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=9:1), so as to obtain the title compound (1.09 g) in the form of a yellow oily substance.

후처리

  1. temperatureunder cooling in an ice bath
  2. stirringThe obtained mixture was stirred for 1 hour
  3. stirringwas then stirred for 2.5 hours
  4. temperatureunder cooling in an ice bath
  5. extractionthe obtained mixture was then extracted with ethyl acetate
  6. washThe organic layer was washed with a saturated saline
  7. dry with materialwas then dried over anhydrous magnesium sulfate
  8. concentrationfollowed by vacuum concentration
  9. customThe residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=9:1)

출처 및 근거

ORD 기록
ord-1e143a062e8842108de2bd636e760884
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642626B2

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