Ethylene carbonate → HCID 22672577、化合物

HRID 1369573ノート

反応式

HRID 1369573 の反応式
[OH:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([CH3:16])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[H-].[Li+].C1(=O)O[CH2:27][CH2:26][O:25]1>CN(C)C=O.[I-].C[N+](C)(C)C>[CH3:15][C:13]1[N:14]=[C:7]2[C:6]([NH:5][CH2:4][C:3]3[C:17]([CH3:21])=[CH:18][CH:19]=[CH:20][C:2]=3[O:1][CH2:27][CH2:26][OH:25])=[CH:11][CH:10]=[CH:9][N:8]2[C:12]=1[CH3:16]

参加物

6

反応物 3

HCID 7303Ethylene carbonateHCID 62714Lithium hydrideHCID 22672646HCID 22672646、化合物

生成物 1

HCID 22672577HCID 22672577、化合物収率 41.2%

試薬・触媒・溶媒 2

HCID 6381Tetramethylammonium iodide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 8-(2-hydroxy-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine (0.14 g, 0.5 mmol) in N,N-dimethylformamide (3 ml) was added lithium hydride (0.004 g, 0.51 mmol) and the mixture was stirred for 10 min at 100° C. Ethylene carbonate (0.055 g, 0.63 mmol) was added and the mixture was stirred for 10 min at 130° C. Tetramethylammonium iodide (0.054 g, 0.63 mmol) was added and the mixture was stirred for 12 h. at 140-145° C. The solvent was evaporated under reduced pressure and the residue was solved in methylene chloride, washed twice with saturated sodium bicarbonate. The organic layer was separated, dried and evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using methylene chloride:methanol (100:6) as eluent to give 0.067 g (41%) of the title compound.

後処理

  1. stirringthe mixture was stirred for 10 min at 130° C
  2. stirringthe mixture was stirred for 12 h. at 140-145° C
  3. customThe solvent was evaporated under reduced pressure
  4. washwashed twice with saturated sodium bicarbonate
  5. customThe organic layer was separated
  6. customdried
  7. customevaporated under reduced pressure
  8. customthe residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-17d3dc67aadc452fb0e5bf52ada6f72e
出典データセット
uspto-grants-2003_06
特許番号
US06579884B1

反応ノート

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