Potassium Carbonate → ethyl 3-(4-nitrophenyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylate

HRID 230546ノート

反応式

HRID 230546 の反応式
C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[NH:10][C:9]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18].[N+:22]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)([O-:24])=[O:23]>O1CCOCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([C:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[NH:10][C:9]=2[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:27][CH:26]=1)([O-:24])=[O:23]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 27735524-Nitrophenylboronic acidHCID 577628443-Bromo-1H-pyrrolo[3,2-B]pyridine-2-carboxylic acid ethyl ester

生成物 1

HCID 57762837ethyl 3-(4-nitrophenyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylate収率 22.5%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

3 g of potassium carbonate and 0.8 g of palladium tetrakis(triphenylphosphine) are added to a solution of 2 g of ethyl 3-bromo-1H-pyrrolo[3,2-b]pyridine-2-carboxylate and 1.5 g of 4-nitrophenylboronic acid in 50 ml of dioxane. The mixture is refluxed for 20 hours, and then filtered. The filtrate is concentrated under reduced pressure and the residue is purified by chromatography on a silica column, elution being carried out with a mixture of cyclohexane and ethyl acetate (50/50 by volume), to give 0.52 g of ethyl 3-(4-nitrophenyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylate, the characteristics of which are as follows:

後処理

  1. temperatureThe mixture is refluxed for 20 hours
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customthe residue is purified by chromatography on a silica column, elution
  5. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (50/50 by volume)

出典と根拠

ORDレコード
ord-570c63974fce4ee6b9052ea3d84d19d1
出典データセット
uspto-grants-2009_07
特許番号
US07566736B2

反応ノート

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