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

HRID 8809

反応式

HRID 8809 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7fd2ced16c8e4fd7949b21830373d6d1
出典データセット
uspto-grants-2006_08
特許番号
US07091216B2

関連ノート

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