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

HRID 550891

反応式

HRID 550891 の反応式
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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 8471Triethylamine溶媒HCID 312751,4-Dioxane溶媒

実験手順

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:

後処理

  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)

出典と根拠

ORDレコード
ord-cb85bc5963f54265acc359ec33f26a0a
出典データセット
uspto-grants-2011_05
特許番号
US07947706B2

関連ノート

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