2-Propanethiol → 2-Isopropylsulfanyl-6-methyl-nicotinic acid methyl ester

HRID 62848

반응식

HRID 62848 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[N:6][C:5]=1Cl.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:19][CH:20]([SH:22])[CH3:21]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[N:6][C:5]=1[S:22][CH:20]([CH3:21])[CH3:19]

참가 물질

5

반응물 3

HCID 63642-PropanethiolHCID 10796Cesium carbonateHCID 13055804Methyl 2-chloro-6-methylpyridine-3-carboxylate

생성물 1

HCID 901181052-Isopropylsulfanyl-6-methyl-nicotinic acid methyl ester수율 69.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2-Chloro-6-methyl-nicotinic acid methyl ester (1.39 g, 7.44 mmol) obtained in Step A was dissolved in DMF (15 mL). Cs2CO3(4.88 g, 14.99 mmol) and propane-2-thiol (1.39 mL, 14.99 mmol) were added to the solution, and the mixture was stirred at room temperature for 2 hours. The reactant was concentrated under reduced pressure to remove the solvent. The residue was added with water and then extracted with EtOAc. The organic layer was dried with MgSO4, filtered and concentrated under reduced pressure. The obtained residue was purified by column chromatography (eluent EtOAc/Hex=1/5) to obtain the title compound (1.17 g, 69%).

후처리

  1. concentrationThe reactant was concentrated under reduced pressure
  2. customto remove the solvent
  3. additionThe residue was added with water
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by column chromatography (eluent EtOAc/Hex=1/5)

출처 및 근거

ORD 기록
ord-7ad44a8f9f314848acf3a650ee093685
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447044B2

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