Ethanol → Ethyl 6-dimethylaminoimidazo[1,2-a]pyridine-2-carboxylate

HRID 1952220ノート

反応式

HRID 1952220 の反応式
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:10][N:11]([CH3:19])[C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[N:16][CH:17]=1.C(O)C>COCCOC>[CH3:10][N:11]([CH3:19])[C:12]1[CH:13]=[CH:14][C:15]2[N:16]([CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:18]=2)[CH:17]=1

参加物

5

反応物 3

HCID 702EthanolHCID 66144Ethyl bromopyruvateHCID 5743468N5,N5-Dimethylpyridine-2,5-diamine

生成物 1

HCID 44124134Ethyl 6-dimethylaminoimidazo[1,2-a]pyridine-2-carboxylate

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
20 °C

実験手順

215 μl of ethyl bromopyruvate are added to a suspension of 0.2 g of 5-dimethylaminopyridine-2-amine in 3 ml of DME. The reaction mixture is stirred at 20° C. for 16 hours, then, after addition of 3 ml of ethanol, for 16 hours at reflux and, finally, concentrated under reduced pressure. The residue is filtered on a cartridge comprising 15 g of silica, elution being carried out with a mixture of dichloromethane and methanol (98/2). The fractions comprising the expected product are combined and washed with a saturated sodium bicarbonate solution. The organic phase is dried and concentrated to dryness under reduced pressure to give 76 mg of ethyl 6-dimethylamino-imidazo[1,2-a]pyridine-2-carboxylate in the form of a green oil used as is in the continuation of the synthesis.

後処理

  1. temperaturefor 16 hours at reflux
  2. concentrationfinally, concentrated under reduced pressure
  3. filtrationThe residue is filtered on a cartridge
  4. wash15 g of silica, elution
  5. additionbeing carried out with a mixture of dichloromethane and methanol (98/2)
  6. washwashed with a saturated sodium bicarbonate solution
  7. customThe organic phase is dried
  8. concentrationconcentrated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-384f31a5c25241b495a09a844000b14a
出典データセット
uspto-grants-2013_03
特許番号
US08404848B2

反応ノート

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