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

HRID 573692ノート

反応式

HRID 573692 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:17]=[C:16](Cl)[N:15]=[C:14]3[S:19][C:20]([CH3:30])=[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=4)[C:13]=23)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=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:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([C:31]#[N:32])[N:15]=[C:14]3[S:19][C:20]([CH3:30])=[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=4)[C:13]=23)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 13901-MethylimidazoleHCID 866718533-Chloro-N-{6-chloro-2-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide

生成物 1

HCID 683241643-Chloro-N-{6-cyano-2-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide

試薬・触媒・溶媒 2

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

反応条件

温度
160 °C

実験手順

To a stirred solution of 3-chloro-N-{6-chloro-2-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide (Example 117) (70 mg, 0.146 mmol) in 1-methylimidazole (1 mL) at RT was added potassium ferrocyanide (12.34 mg, 0.029 mmol) and copper(I) iodide (2.78 mg, 0.015 mmol). The reaction mixture was heated to 160° C. under a nitrogen atmosphere. Extra potassium ferrocyanide (12.34 mg, 0.029 mmol) and copper(I) iodide (2.78 mg, 0.015 mmol) were added and the mixture heated to 180° C. overnight. The reaction mixture was then cooled to RT and purified by normal phase chromatography, eluting with a gradient of 0-40% ethyl acetate in DCM and then further purified by MDAP (acidic conditions), to give the title compound (5 mg). LCMS (A) m/z: 470 [M+1]+, Rt 1.53 min (acidic).

後処理

  1. temperaturethe mixture heated to 180° C. overnight
  2. temperatureThe reaction mixture was then cooled to RT
  3. custompurified by normal phase chromatography
  4. washeluting with a gradient of 0-40% ethyl acetate in DCM
  5. customfurther purified by MDAP (acidic conditions)

出典と根拠

ORDレコード
ord-670e14bca6434ac597b306757e5bc1b0
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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