Hydrochloric Acid → 4'-[[5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridin-3-yl]methyl][1,1'-biphenyl-2-yl]carboxylic acid methyl ester

HRID 248438ノート

反応式

HRID 248438 の反応式
[H-].[Na+].[CH3:3][C:4]1[N:9]=[C:8]2[N:10]=[C:11]([CH2:13][CH3:14])[NH:12][C:7]2=[C:6]([CH3:15])[CH:5]=1.Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:25]([C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:20][CH:19]=1.Cl>CN(C=O)C.O>[CH3:33][O:32][C:30]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:21]1[CH:20]=[CH:19][C:18]([CH2:17][N:10]2[C:8]3=[N:9][C:4]([CH3:3])=[CH:5][C:6]([CH3:15])=[C:7]3[N:12]=[C:11]2[CH2:13][CH3:14])=[CH:23][CH:22]=1)=[O:31]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 98153742,6-Dimethyl-8-ethyl-1-deazapurineHCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylate

生成物 1

HCID 214641284'-[[5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridin-3-yl]methyl][1,1'-biphenyl-2-yl]carboxylic acid methyl ester収率 61%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

To a suspension of sodium hydride (345 mg, 60% in oil, 8.6 mmol) in dry DMF (10 mL) was added 5,7-dimethyl-2-ethylimidazo[4,5-b]pyridine (1.5 g, 8.6 mmol) under an atmosphere of dry nitrogen. The reaction mixture was stirred at room temperature until the evolution of gas subsided. The reaction mixture was cooled to 0° C. and a solution of methyl 4'-bromomethylbiphenyl-2-carboxylate (2.7 g, 8.84 mmol) in dry DMF (5 mL) was added dropwise. The resulting solution was stirred at room temperature overnight. The reaction mixture was poured into water (250 mL), the pH was adjusted to pH 6 by the addition of 1N HCl, and the product was extracted into ethyl acetate. Flash chromatography (silica, ethyl acetate) gave 4'-[[5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridin-3-yl]methyl][1,1'-biphenyl-2-yl]carboxylic acid methyl ester (2.05 g, 61%) as an amorphous solid.

後処理

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringThe resulting solution was stirred at room temperature overnight
  3. extractionthe product was extracted into ethyl acetate

出典と根拠

ORDレコード
ord-547f9e06da10421b8d7dc6bd910a6f81
出典データセット
uspto-grants-1993_05
特許番号
US05210204

反応ノート

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