1,2-Dimethoxyethane → N,N-diallyl-4-(3-(5-chloro-6-methoxypyridin-3-yl)phenylsulfonamido)pyridine-3-sulfonamide

HRID 2283343ノート

反応式

HRID 2283343 の反応式
[CH2:1]([N:4]([CH2:25][CH:26]=[CH2:27])[S:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=1)(=[O:17])=[O:16])(=[O:7])=[O:6])[CH:2]=[CH2:3].[Cl:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[N:33][C:34]=1[O:35][CH3:36].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]([CH2:25][CH:26]=[CH2:27])[S:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:31]2[CH:32]=[N:33][C:34]([O:35][CH3:36])=[C:29]([Cl:28])[CH:30]=2)[CH:19]=1)(=[O:17])=[O:16])(=[O:7])=[O:6])[CH:2]=[CH2:3]

参加物

7

反応物 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 24901777(5-Chloro-6-methoxypyridin-3-yl)boronic acidHCID 57750923N,N-diallyl-4-(3-bromophenylsulfonamido)pyridine-3-sulfonamide

生成物 1

HCID 57750978N,N-diallyl-4-(3-(5-chloro-6-methoxypyridin-3-yl)phenylsulfonamido)pyridine-3-sulfonamide収率 58%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of N,N-diallyl-4-(3-bromophenylsulfonamido)pyridine-3-sulfonamide (0.29 g, 0.62 mmol), 5-chloro-6-methoxypyridin-3-ylboronic acid (0.15 g, 0.81 mmol), (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.026 g, 0.030 mmol), cesium carbonate (0.30 g, 0.93 mmol), 1,2-dimethoxyethane (4.5 mL) and water (0.5 mL) under an atmosphere of argon was heated at 100° C. for 15 min in a microwave reactor. 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 58% 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-fdc6b04dd0de4f7baf7ddd51aadebe30
出典データセット
uspto-grants-2015_09
特許番号
US09145380B2

反応ノート

読み込み中…