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Methanesulfonyl chloride → 5-bromo-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)-2H-indazole-3-carboxamide

HRID 595704
ノート
印刷プレビュー

反応式

HRID 595704 の反応式
[NH2:1][C:2]1[C:3]([Br:22])=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[C:6]=2[C:18]([NH:20][CH3:21])=[O:19].[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl.N1C=CC=CC=1.O>[Br:22][C:3]1[C:2]([NH:1][S:24]([CH3:23])(=[O:26])=[O:25])=[CH:10][C:9]2[C:5](=[C:6]([C:18]([NH:20][CH3:21])=[O:19])[N:7]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[N:8]=2)[CH:4]=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

5

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 903324916-amino-5-bromo-2-(4-fluorophenyl)-N-methyl-2H-indazole-3-carboxamide

生成物 1

HCID 569631675-bromo-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)-2H-indazole-3-carboxamide収率 78%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21875418Pyridine methylene chloride溶媒

反応条件

温度
25 °C

実験手順

To a degassed solution of 6-amino-5-bromo-2-(4-fluorophenyl)-N-methyl-2H-indazole-3-carboxamide (0.75 g, 2.1 mmol) in DCM/Pyridine (10 mL/3 mL) was added MsCl (1.2 g, 10.5 mmol) under N2 at 0° C. for 30 min. The reaction was stirred at 25° C. for 8 hours. The reaction mixture was diluted with water, extracted with EtOAc and washed with brine, and then dried over Na2SO4. After concentration, the residue was purified by column chromatography (PE:EA=2:1) to give crude 5-bromo-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)-2H-indazole-3-carboxamide (0.65 g, yield: 78%). 1H-NMR (CDCl3, 400 MHz) δ 8.30 (s, 1H), 8.03 (s, 1H), 7.56˜7.60 (m, 2H), 7.20˜7.25 (m, 2H), 6.97 (s, 1H), 5.73 (s, 1H), 3.08 (s, 3H), 2.99 (d, J=4.8 Hz, 3H). MS (M+H)+: 441/443.

後処理

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentration
  5. customthe residue was purified by column chromatography (PE:EA=2:1)

出典と根拠

ORDレコード
ord-abd761d8070a430eb99ad01779337185
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09243002B2

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