N-Iodosuccinimide → 8-Chloro-1-iodo-3-methylsulfanyl-imidazo[1,5-a]pyrazine

HRID 449008ノート

反応式

HRID 449008 の反応式
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([S:11][CH3:12])=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1.[I:13]N1C(=O)CCC1=O>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([S:11][CH3:12])=[N:9][C:10]=2[I:13])[CH:5]=[CH:6][N:7]=1

参加物

5

反応物 2

HCID 120273N-IodosuccinimideHCID 591303828-Chloro-3-(methylsulfanyl)imidazo[1,5-A]pyrazine

生成物 1

HCID 589019878-Chloro-1-iodo-3-methylsulfanyl-imidazo[1,5-a]pyrazine収率 94%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
55 °C

実験手順

P To a solution of 8-chloro-3-methylsulfanyl-imidazo[1,5-a]pyrazine (1.75 g, 0.00876 mol) in DMF (15 mL) was added N-iodosuccinimide (3.94 g, 0.0175 mol), the resulting mixture was stirred at 55° C. for 6 hrs. The mixture was diluted with EtOAc (200 mL), washed with sat. aq. NaHCO3 (40 mL), water (2×40 mL), brine (40 mL), and dried over anhydrous sodium sulfate. The crude material was purified by silica gel chromatography to give the title compound as a yellow solid, 2.68 g, 94% yield. 1H NMR (CDCl3, 400 MHz): δ 2.72 (s, 3H), 7.36 (d, J=4.8 Hz, 1H), 7.76 (d, J=4.8 Hz, 1H).

後処理

  1. washwashed with sat. aq. NaHCO3 (40 mL), water (2×40 mL), brine (40 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe crude material was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-87439b1cffb448068234f536f9a05e83
出典データセット
uspto-grants-2013_07
特許番号
US08481733B2

反応ノート

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