Methane → ethyl 3-(4-aminophenyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

HRID 550891

반응식

HRID 550891 반응식
Br[C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].Cl.[NH2:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.[F-].[K+].C>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(N(CC)CC)C>[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[C:10]3[C:5](=[CH:6][N:7]=[CH:8][CH:9]=3)[NH:4][C:3]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:20][CH:19]=1

참가 물질

9

반응물 4

HCID 297MethaneHCID 522689Potassium FluorideHCID 2734614(4-Aminophenyl)boronic acid hydrochlorideHCID 57445353ethyl 3-bromo-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

생성물 1

HCID 57445352ethyl 3-(4-aminophenyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate수율 57.4%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8471Triethylamine용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of 1 g of ethyl 3-bromo-1H-pyrrolo[2,3-c]pyridine-2-carboxylate in 100 mL of dioxane are added 773 mg of 4-aminophenylboronic acid hydrochloride and 1.1 g of potassium fluoride in 9 mL of water. The reaction mixture is stirred under an argon atmosphere for 15 minutes. 425 mg of tetrakis(triphenylphosphine)palladium(0) and 630 μL of triethylamine are added. The reaction mixture is stirred for 17 hours at reflux. After treating with carbon black and then filtering through Celite®, the filtrate is concentrated under reduced pressure. The residue is purified by flash chromatography on a column of silica (60; 35-70 μM), eluting with a mixture of dichloromethane, methanol and acetonitrile (90/5/5 by volume). 600 mg of ethyl 3-(4-aminophenyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate are obtained, the characteristics of which are as follows:

후처리

  1. stirringThe reaction mixture is stirred for 17 hours
  2. temperatureat reflux
  3. filtrationfiltering through Celite®
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe residue is purified by flash chromatography on a column of silica (60; 35-70 μM)
  6. washeluting with a mixture of dichloromethane, methanol and acetonitrile (90/5/5 by volume)

출처 및 근거

ORD 기록
ord-cb85bc5963f54265acc359ec33f26a0a
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947706B2

연결된 노트

불러오는 중…