Cesium carbonate → Methyl 7-(3-aminophenoxy)thieno[3,2-b]pyridine-2-carboxylate

HRID 525827ノート

反応式

HRID 525827 の反応式
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[S:10][C:3]=12.[NH2:15][C:16]1[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=1.CCOC(C1C(=O)CCCC1)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.[Cu]Cl>[NH2:15][C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=1)[O:22][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[S:10][C:3]=12

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 115683-AminophenolHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 59424429Methyl 7-chlorothieno[3,2-B]pyridine-2-carboxylate

生成物 1

HCID 117690318Methyl 7-(3-aminophenoxy)thieno[3,2-b]pyridine-2-carboxylate

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
70 °C

実験手順

A mixture of methyl 7-chlorothieno[3,2-b]pyridine-2-carboxylate (500 mg, 2.20 mmol), 3-aminophenol (330 mg, 3.0 mmol), ethyl 2-cyclohexanonecarboxylate (73 mg, 0.43 mmol), copper(I) chloride (22 mg, 0.22 mmol) and cesium carbonate (1.48 g, 4.55 mmol) in 20 ml of anhydrous DMSO was placed in a 50 ml pressure tube, flushed with nitrogen, sealed and heated at 70° C. for 3 hours. The mixture was cooled to room temperature and poured into 100 ml of water. The precipitates were filtered, washed with water and dried to give crude methyl 7-(3-aminophenoxy)thieno[3,2-b]pyridine-2-carboxylate as brown solid. Yield: 330 mg.

後処理

  1. customwas placed in a 50 ml pressure tube
  2. customflushed with nitrogen
  3. customsealed
  4. temperatureThe mixture was cooled to room temperature
  5. additionpoured into 100 ml of water
  6. filtrationThe precipitates were filtered
  7. washwashed with water
  8. customdried

出典と根拠

ORDレコード
ord-73a3476223924543b82e1e35f2ff9e29
出典データセット
uspto-grants-2016_05
特許番号
US09340555B2

反応ノート

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