Cesium carbonate → Methyl 4-chlorothieno[2,3-c]pyridine-2-carboxylate

HRID 2075331노트

반응식

HRID 2075331 반응식
Cl[C:2]1[CH:9]=[N:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.C([O-])([O-])=O.[Cs+].[Cs+].[SH:17][CH2:18][C:19]([O:21][CH3:22])=[O:20]>CN(C=O)C>[Cl:10][C:6]1[CH:7]=[N:8][CH:9]=[C:2]2[S:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:4][C:3]=12

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 16907Methyl ThioglycolateHCID 27629883,5-Dichloro-4-pyridinecarboxaldehyde

생성물 1

HCID 18516294Methyl 4-chlorothieno[2,3-c]pyridine-2-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

3,5-Dichloroisonicotinaldehyde (20.39 g, 115.8 mmol) obtained from Aldrich was dissolved in 250 mL DMF. To this solution was added Cs2CO3 (12.9 g, 121.59 mmol) and then methyl 2-mercaptoacetate (56.6 g, 173.7 mmol). The mixture was stirred at room temperature for 3 hours. After removing 200 mL DMF under a reduced pressure, the remaining residue was mixed with 100 mL water. After filtration, the filter cake was washed thoroughly with water and air dried. An off-white solid was obtained as the pure product (23.15 g, y=88%). LCMS (API-ES) m/z (%): 228.2 (100%, M++H); 1H NMR (300 MHz, DMSO-d6) δ ppm 3.96 (s, 3H) 8.12 (s, 1H) 8.64 (s, 1H) 9.36 (s, 1H).

후처리

  1. customAfter removing 200 mL DMF under a reduced pressure
  2. additionthe remaining residue was mixed with 100 mL water
  3. filtrationAfter filtration
  4. washthe filter cake was washed thoroughly with water and air
  5. customdried
  6. customAn off-white solid was obtained as the pure product (23.15 g, y=88%)

출처 및 근거

ORD 기록
ord-14d89d8addaf429cbb13a66aa11697cb
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919504B2

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