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

HRID 573618노트

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HRID 573618 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178511492HCID 178511492, 화합물촉매2회

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온도
160 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0a7df37e293941fda35c29fefd006ced
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029545B2

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