Benzenesulfonyl chloride → 4-(2-Chloroethoxy)-1-(phenylsulfonyl)-1H-indazole

HRID 1982794ノート

反応式

HRID 1982794 の反応式
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[N:8][NH:9]2.[H-].[Na+].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[N:8][N:9]2[S:22]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:24])=[O:23]

参加物

5

反応物 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 22326703HCID 22326703、化合物

生成物 1

HCID 120184394-(2-Chloroethoxy)-1-(phenylsulfonyl)-1H-indazole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A stirred solution of 4-(2-chloroethoxy)-1H-indazole (1.1 g, 5.59 mmol) in tetrahydrofuran is treated with NaH (0.335 g, 60% in mineral oil, 8.39 mmol) under nitrogen at room temperature, stirred for 30 minutes, treated with benzenesulfonyl chloride (0.86 ml, 6.71 mmol), stirred at room temperature for 18 hr, quenched with water and diluted with ethyl acetate. The phases are separated and the organic phase is washed with water and brine, dried over MgSO4 and concentrated in vacuo. The resultant residue is purified by flash chromatography (silica gel, EtOAc/hexane: 3/7) to give the desired product as a white solid, 1.75 g (93%), mp 102-104° C., identified by NMR and mass spectral analyses.

後処理

  1. stirringstirred at room temperature for 18 hr
  2. customquenched with water
  3. additiondiluted with ethyl acetate
  4. customThe phases are separated
  5. washthe organic phase is washed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue is purified by flash chromatography (silica gel, EtOAc/hexane: 3/7)

出典と根拠

ORDレコード
ord-ded6b563ca714189becc6875d3d8a529
出典データセット
uspto-grants-2009_06
特許番号
US07541358B2

反応ノート

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