Triethylamine → Methyl thieno[2,3-b]pyridine-2-carboxylate

HRID 1691554

반응식

HRID 1691554 반응식
Cl[C:2]1[C:7]([CH:8]=O)=[CH:6][CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[C:17]([O:21][CH3:22])(=[O:20])[CH2:18][SH:19]>CC#N>[CH3:22][O:21][C:17]([C:18]1[S:19][C:2]2=[N:3][CH:4]=[CH:5][CH:6]=[C:7]2[CH:8]=1)=[O:20]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 16907Methyl ThioglycolateHCID 7376072-Chloro-3-pyridinecarboxaldehyde

생성물 1

HCID 19007380Methyl thieno[2,3-b]pyridine-2-carboxylate수율 29%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To 2-chloro-3-pyridine carboxaldehyde, compound 147-A, (5.07 g, 35.8 mmol), dissolved in MeCN (30 mL) was added triethylamine (6.5 mL, 46.5 mmol) followed by methyl thioglycolate (3.49 mL, 38.3 mmol) and the reaction was refluxed for 18 h. The reaction mixture was cooled and the solvent evaporated under reduced pressure. The crude residue was partitioned between H2O and EtOAc, the layers separated and the aqueous phase extracted with EtOAc. The organic layers were combined, washed with H2O, brine, dried over Na2SO4, filtered, and the solvent evaporated under reduced pressure. The crude residue was purified by flash column chromatography (SiO2) eluting with a heptane-EtOAc gradient to afford compound 147-B as a white solid (2.01 g, 29%). 1H-NMR (DMSO-d6): δ 3.91 (s, 3H), 7.54-7.57 (m, 1H), 8.23 (s, 1H), 8.43-8.46 (m, 1H), 8.72-8.74 (m, 1H); MS: m/z 194.1 (MH+).

후처리

  1. temperaturethe reaction was refluxed for 18 h
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent evaporated under reduced pressure
  4. customThe crude residue was partitioned between H2O and EtOAc
  5. customthe layers separated
  6. extractionthe aqueous phase extracted with EtOAc
  7. washwashed with H2O, brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customthe solvent evaporated under reduced pressure
  11. customThe crude residue was purified by flash column chromatography (SiO2)
  12. washeluting with a heptane-EtOAc gradient

출처 및 근거

ORD 기록
ord-c1afafce3c3e442d9dd52a74565545dc
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153682B2

연결된 노트

불러오는 중…