Cesium carbonate → Methyl 6-(2-chlorophenyl)-5-(4-chlorophenyl)-2-(3,3-dimethyl-2-oxobutoxy)nicotinate

HRID 8809

반응식

HRID 8809 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:13][C:12](=[O:14])[C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:10][C:9]=1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[CH:10][C:11]([C:15]([O:17][CH3:18])=[O:16])=[C:12]([O:14][CH2:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])[N:13]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 21642BromopinacoloneHCID 21984816Methyl 6-(2-chlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

생성물 1

HCID 21984933Methyl 6-(2-chlorophenyl)-5-(4-chlorophenyl)-2-(3,3-dimethyl-2-oxobutoxy)nicotinate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A 25 mL rb flask was charged with 1.111 g (2.97 mmol) of the product of Step B, 1.451 g (4.45 mmol) Cs2CO3, 10 mL DMF and finally 0.5 mL (3.71 mmol) of bromopinacolone. The reaction mixture was stirred at room temperature 1 h then partitioned between EtOAc and water. The organic layer was washed with water, brine, then dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 0–20% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound.

후처리

  1. customthen partitioned between EtOAc and water
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified on a silica gel flash chromatography column
  7. washeluted with 0–20% EtOAc-hexane
  8. customEvaporation of the purified fractions
  9. customdrying in vacuo

출처 및 근거

ORD 기록
ord-7fd2ced16c8e4fd7949b21830373d6d1
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091216B2

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