ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Iodoethane → N-[3-(4-bromo-1-ethyl-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluoro-N-(2-methoxy-ethoxymethyl)-benzenesulfonamide

HRID 45898
ノート
印刷プレビュー

反応式

HRID 45898 の反応式
[Br:1][C:2]1[C:3]([C:7]2[C:8]([F:32])=[C:9]([N:14]([CH2:26][O:27][CH2:28][CH2:29][O:30][CH3:31])[S:15]([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])(=[O:17])=[O:16])[CH:10]=[CH:11][C:12]=2[F:13])=[N:4][NH:5][CH:6]=1.[OH-].[Na+].[CH2:35](I)[CH3:36]>C(Cl)Cl.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[Br:1][C:2]1[C:3]([C:7]2[C:8]([F:32])=[C:9]([N:14]([CH2:26][O:27][CH2:28][CH2:29][O:30][CH3:31])[S:15]([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])(=[O:17])=[O:16])[CH:10]=[CH:11][C:12]=2[F:13])=[N:4][N:5]([CH2:35][CH3:36])[CH:6]=1.[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH2:35][CH3:36])[C:3]=1[C:7]1[C:8]([F:32])=[C:9]([N:14]([CH2:26][O:27][CH2:28][CH2:29][O:30][CH3:31])[S:15]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])(=[O:17])=[O:16])[CH:10]=[CH:11][C:12]=1[F:13]
参加物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 6340IodoethaneHCID 14798Sodium HydroxideHCID 178496268HCID 178496268、化合物

生成物 2

HCID 67183880N-[3-(4-bromo-1-ethyl-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluoro-N-(2-methoxy-ethoxymethyl)-benzenesulfonamide収率 50%HCID 67185634N-[3-(4-bromo-2-ethyl-2H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluoro-N-(2-methoxy-ethoxymethyl)-benzenesulfonamide
収率 26%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

N-[3-(4-bromo-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluoro-N-(2-methoxy-ethoxymethyl)-benzenesulfonamide (584 mg, 1.085 mmol) was dissolved in DCM (5 mL). 32% sodium hydroxide was added (5 mL) followed by ethyl iodide (0.13 mL, 1.628 mmol, 1.5 eq) and TBAB (58 mg, 0.18 mmol, 0.17 eq) and the biphasic mixture was vigorously stirred at room temperature for 3 hours. The reaction mixture was then diluted with DCM, washed with water and brine, dried over Na2SO4 and evaporated to dryness. The two ethyl pyrazole regioisomers have been separated by chromatography on silica gel (n-hexane/ethyl acetate 7:3): 308 mg (50% yield) of the desired regioisomer N-[3-(4-bromo-1-ethyl-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluoro-N-(2-methoxy-ethoxymethyl)-benzenesulfonamide were obtained along with 160 mg (26% yield) of the minor regioisomer N-[3-(4-bromo-2-ethyl-2H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluoro-N-(2-methoxy-ethoxymethyl)-benzenesulfonamide.

後処理

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness
  4. customThe two ethyl pyrazole regioisomers have been separated by chromatography on silica gel (n-hexane/ethyl acetate 7:3)

出典と根拠

ORDレコード
ord-8fed6ec6877c4066ae8d657809d139c9
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08541575B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート