2-Fluoro-4-nitrophenol → 7-(2-Fluoro-4-nitrophenoxy)-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)thieno[3,2-b]pyridine

HRID 1261226ノート

反応式

HRID 1261226 の反応式
Cl[C:2]1[C:3]2[S:10][C:9]([C:11]3[N:12]=[CH:13][N:14]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:15]=3)=[CH:8][C:4]=2[CH:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[K+].[K+].[F:30][C:31]1[CH:36]=[C:35]([N+:37]([O-:39])=[O:38])[CH:34]=[CH:33][C:32]=1[OH:40]>C1(OC2C=CC=CC=2)C=CC=CC=1.C(Cl)Cl>[F:30][C:31]1[CH:36]=[C:35]([N+:37]([O-:39])=[O:38])[CH:34]=[CH:33][C:32]=1[O:40][C:4]1[CH:5]=[CH:6][N:7]=[C:2]2[CH:8]=[C:9]([C:11]3[N:12]=[CH:13][N:14]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:21])([CH3:22])[CH3:23])[CH:15]=3)[S:10][C:3]=12

参加物

6

反応物 3

HCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 866445877-Chloro-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)thieno[3,2-d]pyridine

生成物 1

HCID 594245697-(2-Fluoro-4-nitrophenoxy)-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)thieno[3,2-b]pyridine収率 61%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 7583Diphenyl Ether溶媒

実験手順

A suspension of 91 (4.2 g, 11.5 mmol), potassium carbonate (7.95 g, 57.5 mmol) and 2-fluoro-4-nitrophenol (4.97 g, 31.6 mmol) was heated at 190° C. in diphenyl ether (15 ml) for 4.5 hrs, cooled to room temperature, diluted with DCM and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography (eluents hexane and acetone/hexane, 45:55) to afford title compound 92 (3.4 mg, 61% yield) as a yellow solid MS (m/z) 487.0 (M+H).

後処理

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. custompurified by column chromatography (eluents hexane and acetone/hexane, 45:55)

出典と根拠

ORDレコード
ord-ea20d4f5152e4e55af08470d4a5e433a
出典データセット
uspto-grants-2013_06
特許番号
US08470850B2

反応ノート

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