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

HRID 525827노트

반응식

HRID 525827 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 62652Cuprous chloride촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-73a3476223924543b82e1e35f2ff9e29
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340555B2

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