Bromine → 4-(3-bromoimidazo[1,2-a]pyrimidin-6-yl)-2-fluoro-N-methylbenzamide

HRID 1257788ノート

反応式

HRID 1257788 の反応式
[Br:1]Br.C([O-])(=O)C.[Na+].[F:8][C:9]1[CH:18]=[C:17]([C:19]2[CH:20]=[N:21][C:22]3[N:23]([CH:25]=[CH:26][N:27]=3)[CH:24]=2)[CH:16]=[CH:15][C:10]=1[C:11]([NH:13][CH3:14])=[O:12]>C(O)(=O)C>[Br:1][C:25]1[N:23]2[CH:24]=[C:19]([C:17]3[CH:16]=[CH:15][C:10]([C:11]([NH:13][CH3:14])=[O:12])=[C:9]([F:8])[CH:18]=3)[CH:20]=[N:21][C:22]2=[N:27][CH:26]=1

参加物

5

反応物 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 672248512-fluoro-4-imidazo[1,2-a]pyrimidin-6-yl-N-methylbenzamide

生成物 1

HCID 672244434-(3-bromoimidazo[1,2-a]pyrimidin-6-yl)-2-fluoro-N-methylbenzamide収率 88.6%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

Bromine (17.4 mL, 0.338 mmol) was added to a mixture of sodium acetate (40.3 mg, 0.491 mmol) and 2-fluoro-4-imidazo[1,2-a]pyrimidin-6-yl-N-methylbenzamide (83.0 mg, 0.307 mmol) in acetic acid (2.6 mL) and the reaction mixture was stirred at ambient temperature for 30 min. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate and brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel with ethyl acetate in dichloromethane (0-50%) to afford the desired product (95 mg, 88.6%). LCMS: (M+H)=348.8/350.9.

後処理

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel with ethyl acetate in dichloromethane (0-50%)

出典と根拠

ORDレコード
ord-7583044ab9c14e1daba8458064286818
出典データセット
uspto-grants-2013_06
特許番号
US08461330B2

反応ノート

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