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

Bromine → (S)-6-(4-bromo-3-cyano-1-cyclobutyl-6 (difluoromethoxy)-5-fluoro-1H-indol-2-yl)-N-(1,1,1-trifluoropropan-2-yl)pyridine-3-sulfonamide

HRID 1028027
ノート
印刷プレビュー

反応式

HRID 1028027 の反応式
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:13][CH:14]([F:16])[F:15])=[C:9]([F:12])[CH:10]=2)[N:5]([CH:17]2[CH2:20][CH2:19][CH2:18]2)[C:4]=1[C:21]1[N:26]=[CH:25][C:24]([S:27]([NH:30][C@@H:31]([CH3:36])[C:32]([F:35])([F:34])[F:33])(=[O:29])=[O:28])=[CH:23][CH:22]=1)#[N:2].[Br:37]Br.OS([O-])=O.[Na+]>[Fe].ClCCCl>[Br:37][C:10]1[C:9]([F:12])=[C:8]([O:13][CH:14]([F:15])[F:16])[CH:7]=[C:6]2[C:11]=1[C:3]([C:1]#[N:2])=[C:4]([C:21]1[N:26]=[CH:25][C:24]([S:27]([NH:30][C@@H:31]([CH3:36])[C:32]([F:34])([F:35])[F:33])(=[O:28])=[O:29])=[CH:23][CH:22]=1)[N:5]2[CH:17]1[CH2:18][CH2:19][CH2:20]1
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

6

反応物 3

HCID 24408BromineHCID 23665763Sodium BisulfiteHCID 71607028(S)-6-(3-cyano-1-cyclobutyl-6-(difluoromethoxy)-5-fluoro-1H-indol-2-yl)-N-(1,1,1-trifluoropropan-2-yl)pyridine-3-sulfonamide

生成物 1

HCID 86668143(S)-6-(4-bromo-3-cyano-1-cyclobutyl-6 (difluoromethoxy)-5-fluoro-1H-indol-2-yl)-N-(1,1,1-trifluoropropan-2-yl)pyridine-3-sulfonamide収率 46.3%

試薬・触媒・溶媒 2

HCID 23925
Iron
触媒
HCID 111,2-Dichloroethane溶媒

反応条件

温度
50 °C

実験手順

A mixture of (S)-6-(3-cyano-1-cyclobutyl-6-(difluoromethoxy)-5-fluoro-1H-indol-2-yl)-N-(1,1,1-trifluoropropan-2-yl)pyridine-3-sulfonamide (500 mg, 0.94 mmol), Fe powder (700 mg, 13 mmol), Br2 (300 μL, 5.9 mmol), and 1,2-dichloroethane (3 mL) was heated at 50° C. for 3 hours. The reaction mixture was then poured into aq. NaHSO3 solution. This was extracted into CH2Cl2. The organic layer was dried over MgSO4 and filtered, and the filtrate was concentrated under vacuum. Purification by silica gel chromatography (ethyl acetate in hexanes, 20% to 30%) yielded (S)-6-(4-bromo-3-cyano-1-cyclobutyl-6 (difluoromethoxy)-5-fluoro-1H-indol-2-yl)-N-(1,1,1-trifluoropropan-2-yl)pyridine-3-sulfonamide (266 mg, 46%) as a white solid.

後処理

  1. extractionThis was extracted into CH2Cl2
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under vacuum
  5. customPurification by silica gel chromatography (ethyl acetate in hexanes, 20% to 30%)

出典と根拠

ORDレコード
ord-7dc2258f4f0542ec90a444b0eaa2e784
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08735414B2

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