N-Methoxy-N-methyl-6-(4-trifluoromethyl-phenyl)-nicotinamide → 4,4,4-Trifluoro-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-butan-1-one

HRID 1669304노트

반응식

HRID 1669304 반응식
CON(C)[C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:7][CH:6]=1.[F:23][C:24]([F:31])([F:30])[CH:25]([Mg]Br)[CH2:26]C>O1CCCC1>[F:23][C:24]([F:31])([F:30])[CH2:25][CH2:26][C:4]([C:5]1[CH:6]=[N:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)=[O:21]

참가 물질

4

반응물 2

HCID 86620355N-Methoxy-N-methyl-6-(4-trifluoromethyl-phenyl)-nicotinamideHCID 178456054HCID 178456054, 화합물

생성물 1

HCID 860853424,4,4-Trifluoro-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-butan-1-one수율 80.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

N-Methoxy-N-methyl-6-(4-trifluoromethyl-phenyl)-nicotinamide (2.0 g, 6.45 mmol) is suspended in anhydrous tetrahydrofuran (25.0 mL), and cooled to 0° C. with stirring under nitrogen. 1,1,1-Trifluoro-butyl magnesium bromide (11.3 mL, 1.14M in tetrahydrofuran, 12.9 mmol) is slowly added to the reaction over 1 h. The reaction is allowed to warm slowly to room temperature and monitored by TLC. Upon complete consumption of starting material, the reaction is carefully acidified with 1N hydrochloric acid, extracted with diethyl ether, washed, dried, and concentrated. The 4,4,4-Trifluoro-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-butan-1-one (1.80 g, 5.19 mmol) 80% yield, is used without further purification.

후처리

  1. temperatureto warm slowly to room temperature
  2. customUpon complete consumption of starting material
  3. extractionextracted with diethyl ether
  4. washwashed
  5. customdried
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6362fe5d99a04a9caa8135b5e23f2cb7
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989457B2

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