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Sodium Carbonate → 2-Methyl-1-(phenylsulfonyl)-5-(3-pyridyl)-1H-pyrrole-3-carbaldehyde

HRID 554347
ノート
印刷プレビュー

反応式

HRID 554347 の反応式
Br[C:2]1[N:6]([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:9])=[O:8])[C:5]([CH3:16])=[C:4]([CH:17]=[O:18])[CH:3]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21](B(O)O)[CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[CH3:16][C:5]1[N:6]([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:9])=[O:8])[C:2]([C:21]2[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=2)=[CH:3][C:4]=1[CH:17]=[O:18]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 862327655-Bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde

生成物 1

HCID 866207692-Methyl-1-(phenylsulfonyl)-5-(3-pyridyl)-1H-pyrrole-3-carbaldehyde収率 72%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物
触媒
HCID 962Water溶媒2 回
HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

Under an argon atmosphere, a suspension of 5-bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde (497 mg), 3-pyridineboronic acid (376 mg), sodium carbonate (481 mg) and tetrakis(triphenylphosphine)palladium (89.2 mg) in 1,2-dimethoxyethane (12 mL) and water (6 mL) was stirred at 80° C. for 1 hr. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, filtrated, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:4) to give the title compound as a white solid (yield 353 mg, 72%).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:4)

出典と根拠

ORDレコード
ord-892bf8fef35e4fa8ad9d6b51ccf3e582
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08048909B2

反応ノート

読み込み中…

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