Sodium hydride → ethyl 2-[4-(1-ethyl-6-methyl-2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)phenoxy]imidazo[1,2-a]pyridine-3-carboxylate

HRID 82645ノート

反応式

HRID 82645 の反応式
Cl[C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[CH2:16]([N:18]1[C:26]2[C:21](=[N:22][CH:23]=[C:24]([CH3:27])[CH:25]=2)[N:20]([C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)[C:19]1=[O:35])[CH3:17].[H-].[Na+].C([O-])(O)=O.[Na+]>COCCOC>[CH2:16]([N:18]1[C:26]2[C:21](=[N:22][CH:23]=[C:24]([CH3:27])[CH:25]=2)[N:20]([C:28]2[CH:33]=[CH:32][C:31]([O:34][C:2]3[N:3]=[C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][N:5]4[C:10]=3[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:30][CH:29]=2)[C:19]1=[O:35])[CH3:17]

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 21643308Ethyl 2-chloroimidazo[1,2-a]pyridine-3-carboxylateHCID 585776031-ethyl-3-(4-hydroxyphenyl)-6-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

生成物 1

HCID 58577566ethyl 2-[4-(1-ethyl-6-methyl-2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)phenoxy]imidazo[1,2-a]pyridine-3-carboxylate収率 12.1%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
50 °C

実験手順

The mixture of ethyl 2-chloroimidazo[1,2-a]pyridine-3-carboxylate (504 mg), 1-ethyl-3-(4-hydroxyphenyl)-6-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (302 mg) and NaH (67.3 mg) in DME (4 mL) was heated at 50° C. for 1 h. The mixture was heated at 200° C. for 3 h under microwave irradiation. The mixture was poured into sat. NaHCO3, and the mixture was extracted with EtOAc. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, EtOAc/hexane) to give the title compound (62.0 mg) as a white solid.

後処理

  1. temperatureThe mixture was heated at 200° C. for 3 h under microwave irradiation
  2. extractionthe mixture was extracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (silica gel, EtOAc/hexane)

出典と根拠

ORDレコード
ord-89d0ab99bb844c67b4997ec263974a67
出典データセット
uspto-grants-2014_09
特許番号
US08846713B2

反応ノート

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