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

HRID 230546노트

반응식

HRID 230546 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

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:

후처리

  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)

출처 및 근거

ORD 기록
ord-570c63974fce4ee6b9052ea3d84d19d1
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566736B2

반응 노트

불러오는 중…