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

HRID 1441350ノート

反応式

HRID 1441350 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
27.5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3ed41b8faf464e009daaa8d9aa2d56f2
出典データセット
uspto-grants-2010_02
特許番号
US07655652B2

反応ノート

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