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

HRID 2075331ノート

反応式

HRID 2075331 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-14d89d8addaf429cbb13a66aa11697cb
出典データセット
uspto-grants-2011_04
特許番号
US07919504B2

反応ノート

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