Sodium sulfide nonahydrate → 2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-thiol

HRID 923767ノート

反応式

HRID 923767 の反応式
[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:19]([CH3:20])[C:13]2=[N:14][CH:15]=[C:16](I)[CH:17]=[C:12]2[N:11]=1)[CH3:2].O.O.O.O.O.O.O.O.O.[S-2:30].[Na+].[Na+].O.[Cl-].[NH4+]>[Cu](I)I.CN(C=O)C>[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:19]([CH3:20])[C:13]2=[N:14][CH:15]=[C:16]([SH:30])[CH:17]=[C:12]2[N:11]=1)[CH3:2]

参加物

6

反応物 3

HCID 73972Sodium sulfide nonahydrateHCID 57429219Ammonium chloride monohydrateHCID 679815902-(2-ethylsulfanyl-phenyl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine

生成物 1

HCID 680912052-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-thiol収率 25.9%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

To a mixture of 2-(2-ethylsulfanyl-phenyl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine (430 mg), copper iodide (229 mg), and DMF (3 ml), sodium sulfide nonahydrate (721 mg) was added at room temperature. The mixture was stirred with heating at 110° C. for 6 hours. Into the reaction mixture cooled to room temperature, saturated aqueous ammonium chloride water solution was poured, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 85 mg of 2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-thiol (hereinafter referred to as Present Compound 145):

後処理

  1. additionwas added at room temperature
  2. temperatureInto the reaction mixture cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-ed1a9a2cc3744f8d92b26f8c75b0fb81
出典データセット
uspto-grants-2016_03
特許番号
US09278983B2

反応ノート

読み込み中…