Selectfluor → (2Z)-3-(dimethylamino)-2-fluoro-1-(1-isopropyl-2-methyl-1H-imidazol-5-yl)prop-2-en-1-one

HRID 1441350노트

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HRID 1441350 반응식
[CH3:1][N:2]([CH3:16])/[CH:3]=[CH:4]/[C:5]([C:7]1[N:11]([CH:12]([CH3:14])[CH3:13])[C:10]([CH3:15])=[N:9][CH:8]=1)=[O:6].[B-](F)(F)(F)[F:18].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CO>[CH3:16][N:2]([CH3:1])/[CH:3]=[C:4](\[F:18])/[C:5]([C:7]1[N:11]([CH:12]([CH3:13])[CH3:14])[C:10]([CH3:15])=[N:9][CH:8]=1)=[O:6]

참가 물질

4

반응물 2

HCID 2724933SelectfluorHCID 22273494(E)-3-(Dimethylamino)-1-(1-isopropyl-2-methyl-1H-imidazol-5-yl)prop-2-en-1-one

생성물 1

HCID 58127046(2Z)-3-(dimethylamino)-2-fluoro-1-(1-isopropyl-2-methyl-1H-imidazol-5-yl)prop-2-en-1-one

시약·촉매·용매 1

HCID 887Methanol용매

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온도
27.5 °C

실험 절차

To a stirred solution of (2E)-3-(dimethylamino)-1-(1-isopropyl-2-methyl-1H-imidazol-5-yl)prop-2-en-1-one, (Method 24 of WO 03/076436; 5.53 g, 25 mmol) in MeOH (100 ml) at ambient temperature, was added in portions over 5 mins, Selectfluor (14.16 g, 40 mmol). The temperature was maintained at 25-30° C. by slight cooling. After stirring for 90 min the reaction mixture was cooled in ice/acetone and filtered. The filtrate was evaporated under reduced pressure and the residue was taken into DCM. It was washed with aq. ammonia, brine, dried over anhydrous Na2SO4 and evaporated under reduced pressure. The title compound was isolated by MPLC on silica gel using two separate columns (10% EtOH/EtOAc, then 3.5% EtOH/DCM) as a golden viscose oil, which crystallized on standing over several weeks. Yield=2.50 g (42%). NMR (300 Mz): 1.40 (d, 6H), 2.38 (s, 3H), 3.05 (s, 6H), 4.70 (septet, 1H), 6.96 (d, 1H), 7.08 (s, 1H); 19F NMR (376 MHz): −166.7 (d); m/z 240.

후처리

  1. filtrationfiltered
  2. customThe filtrate was evaporated under reduced pressure
  3. washIt was washed with aq. ammonia, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-3ed41b8faf464e009daaa8d9aa2d56f2
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07655652B2

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