2-Mesitylenesulfonyl chloride → 6-iodo-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indazole

HRID 724356

反応式

HRID 724356 の反応式
[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].[C:17]1([CH3:29])[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:18]=1[S:25](Cl)(=[O:27])=[O:26]>C1COCC1>[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[S:25]([C:18]2[C:19]([CH3:24])=[CH:20][C:21]([CH3:23])=[CH:22][C:17]=2[CH3:29])(=[O:27])=[O:26])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 130462-Mesitylenesulfonyl chlorideHCID 129912416-iodo-1H-indazoleHCID 23676156Sodium t-butoxide

生成物 1

HCID 218773966-iodo-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indazole収率 100%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
23 °C

実験手順

To a solution of 6-iodo-1H-indazole (7.35 g, 30.1 mmol, 1 equiv) in THF (100 mL) cooled to 0° C. under argon, was added sodium t-butoxide (2.89 g, 30.1 mmol, 1 equiv). A color change from orange to red was observed. Mesitylenesulfonyl chloride (6.60 g, 30.1 mmol, 1 equiv) was added in one portion and the ice bath was removed allowing the reaction mixture to warm to 23° C. After 40 min the mixture was quenched with saturated ammonium chloride and partitioned between water and ethyl acetate. The aqueous was extracted a total of 3 times with ethyl acetate. The combined organic material was washed with brine, dried over sodium sulfate and concentrated under reduced pressure to give 6-iodo-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indazole as an orange solid (12.8 g, 100% yield, 2:1 mixture). 1H NMR (CDCl3) 8.51 (s, 1H), 7.95 (s, 0.66H, major isomer), 7.91 (s, 0.33H, minor isomer), 7.47 (d, 0.33H, J=8.4 Hz), 7.29 (d, 0.33H, J=8.4 Hz), 7.26 (d, 0.66H, J=8.9 Hz), 7.18 (d, 0.66H, 8.9 Hz), 6.84 (s, 2H), 2.51 (s, 6H), 2.15 (s, 3H).

後処理

  1. customthe ice bath was removed
  2. customAfter 40 min the mixture was quenched with saturated ammonium chloride
  3. custompartitioned between water and ethyl acetate
  4. extractionThe aqueous was extracted a total of 3 times with ethyl acetate
  5. washThe combined organic material was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-153a6a18c8654f528761d9f9e022dbcb
出典データセット
uspto-grants-2006_11
特許番号
US07141587B2

関連ノート

読み込み中…