Ethyl 3-formylimidazo[1,2-a]pyridine-2-carboxylate → Ethyl 3-[(2,5-dimethoxyphenyl)hydroxymethyl]-imidazolo[1,2-a]pyridine-2-carboxylate

HRID 2229205ノート

反応式

HRID 2229205 の反応式
[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:2].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[Mg]Br>C1COCC1.C([O-])(O)=O.[Na+]>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[CH:1]([OH:2])[C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

参加物

5

反応物 2

HCID 10704014Ethyl 3-formylimidazo[1,2-a]pyridine-2-carboxylateHCID 178492591HCID 178492591、化合物

生成物 1

HCID 18466904Ethyl 3-[(2,5-dimethoxyphenyl)hydroxymethyl]-imidazolo[1,2-a]pyridine-2-carboxylate収率 57%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 516892Sodium Bicarbonate溶媒

実験手順

A solution of 872 mg (4.0 mmol) of ethyl 3-formyl-imidazolo[1,2-a]pyridine-2-carboxylate in 40 mL THF is treated at −50° C. with 4 mL (4.0 mmol) 1M 2,5-dimethoxyphenylmagnesium bromide in THF. The temperature is allowed to reach −10° C. over 3 hr, diluted with 25 mL sat. NaHCO3 and extracted with 3×50 mL ethyl acetate. The combined organics are washed with 50 mL water and 50 mL brine. The resulting organic layer is dried over anhydrous MgSO4 and the solvent removed in vacuo. The residue is flash chromatographed with 1% methanol in dichloromethane to afford 800 mg (57%) ethyl 3-[(2,5-dimethoxyphenyl)hydroxymethyl]-imidazolo[1,2-a]pyridine-2-carboxylate.

後処理

  1. extractionextracted with 3×50 mL ethyl acetate
  2. washThe combined organics are washed with 50 mL water and 50 mL brine
  3. dry with materialThe resulting organic layer is dried over anhydrous MgSO4
  4. customthe solvent removed in vacuo
  5. customchromatographed with 1% methanol in dichloromethane

出典と根拠

ORDレコード
ord-e572c8631e11486786ca70a1b58f44aa
出典データセット
uspto-grants-2002_07
特許番号
US06420365B1

反応ノート

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