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1,2-Dimethoxyethane → (E)-N,N-Diallyl-4-(2-(4-(benzofuran-2-yl)phenyl)vinylsulfonamido)pyridine-3-sulfonamide

HRID 2283346
ノート
印刷プレビュー

反応式

HRID 2283346 の反応式
[CH2:1]([N:4]([CH2:27][CH:28]=[CH2:29])[S:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH:14][S:15](/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=1)(=[O:17])=[O:16])(=[O:7])=[O:6])[CH:2]=[CH2:3].[O:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[CH:32]=[C:31]1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+].COCCOC>Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[CH2:1]([N:4]([CH2:27][CH:28]=[CH2:29])[S:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH:14][S:15](/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23]([C:31]2[O:30][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[CH:32]=2)=[CH:22][CH:21]=1)(=[O:17])=[O:16])(=[O:7])=[O:6])[CH:2]=[CH2:3]
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 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 2776266Benzo[b]furan-2-boronic acidHCID 57751063(E)-N,N-diallyl-4-(2-(4-bromophenyl)vinylsulfonamido)pyridine-3-sulfonamide

生成物 1

HCID 57751062(E)-N,N-Diallyl-4-(2-(4-(benzofuran-2-yl)phenyl)vinylsulfonamido)pyridine-3-sulfonamide収率 38%

試薬・触媒・溶媒 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

A mixture of (E)-N,N-diallyl-4-(2-(4-bromophenyl)vinylsulfonamido)pyridine-3-sulfonamide (0.47 g, 0.94 mmol), 2-benzofuranboronic acid (0.20 g, 1.23 mmol), (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.039 g, 0.050 mmol), cesium carbonate (0.46 g, 1.41 mmol), 1,2-dimethoxyethane (9 mL) and water (1 mL) under an atmosphere of argon was heated at 120° C. for 15 min in a microwave. The reaction mixture was partitioned between ethyl acetate and diluted hydrochloric acid, the organic phase was dried over magnesium sulfate and the solvent was evaporated. Purification by column chromatography, using chloroform/methanol (98:2) as the eluent, gave the title compound in 38% yield.

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and diluted hydrochloric acid
  2. dry with materialthe organic phase was dried over magnesium sulfate
  3. customthe solvent was evaporated
  4. customPurification by column chromatography

出典と根拠

ORDレコード
ord-dac5a752ba8244489d61bc0f2f0a4de4
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09145380B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート