1-Methylimidazole → 3-Chloro-N-{2-cyano-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-benzenesulfonamide

HRID 573618ノート

反応式

HRID 573618 の反応式
Br[C:2]1[S:22][C:5]2=[N:6][C:7]([CH3:21])=[CH:8][C:9]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)(=[O:13])=[O:12])=[C:4]2[C:3]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=1.[CH3:31][N:32]1C=CN=C1>[Fe-4](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+].[K+].[Cu]I>[Cl:20][C:16]1[CH:15]=[C:14]([S:11]([NH:10][C:9]2[CH:8]=[C:7]([CH3:21])[N:6]=[C:5]3[S:22][C:2]([C:31]#[N:32])=[C:3]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=4)[C:4]=23)(=[O:13])=[O:12])[CH:19]=[CH:18][CH:17]=1

参加物

5

反応物 2

HCID 13901-MethylimidazoleHCID 53250396N-{2-Bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide

生成物 1

HCID 683240723-Chloro-N-{2-cyano-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-benzenesulfonamide収率 74.8%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178511492HCID 178511492、化合物触媒2 回

反応条件

温度
160 °C

実験手順

Alternatively, a mixture of N-{2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide (310 mg, 0.592 mmol) (Example 33), potassium ferrocyanide (50.0 mg, 0.118 mmol), copper(I) iodide (11.27 mg, 0.059 mmol) in 1-methylimidazole (3 mL, 37.6 mmol) was heated at 160° C. for 2 h. Extra potassium ferrocyanide (100 mg, 0.118 mmol) was added and heating continued at 160° C. for 21 h. The mixture was then cooled to RT. Purification by chromatography on silica gel, eluting with a gradient of 0-60% ethyl acetate in cyclohexane, afforded the title compound (208 mg).

後処理

  1. temperatureheating
  2. temperatureThe mixture was then cooled to RT
  3. customPurification by chromatography on silica gel
  4. washeluting with a gradient of 0-60% ethyl acetate in cyclohexane

出典と根拠

ORDレコード
ord-0a7df37e293941fda35c29fefd006ced
出典データセット
uspto-grants-2015_05
特許番号
US09029545B2

反応ノート

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