Dichloromethane → N-cyclohexyl-N-thiazol-2-yl-1-(2-chlorobenzoyl)-5-hydroxy-2-methylindole-3-acetamide

HRID 2219672

反応式

HRID 2219672 の反応式
[CH:1]1([N:7]([C:32]2[S:33][CH:34]=[CH:35][N:36]=2)[C:8](=[O:31])[CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19]C)[CH:17]=3)[N:12]([C:21](=[O:29])[C:22]3[CH:27]=[CH:26][C:25](Cl)=[CH:24][CH:23]=3)[C:11]=2[CH3:30])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br.[Cl:41]CCl>>[CH:1]1([N:7]([C:32]2[S:33][CH:34]=[CH:35][N:36]=2)[C:8](=[O:31])[CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([OH:19])[CH:17]=3)[N:12]([C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:41])[C:11]=2[CH3:30])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

4

反応物 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 58618036N-cyclohexyl-N-thiazol-2-yl-1-(4-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetamide

生成物 1

HCID 69311092N-cyclohexyl-N-thiazol-2-yl-1-(2-chlorobenzoyl)-5-hydroxy-2-methylindole-3-acetamide

実験手順

To a solution of 2 g (3.83 mmol) of N-Cyclohexyl-N-thiazol-2-yl-1-(4-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetamide in 20 mL of anhydrous dichloromethane under nitrogen at −78° C. was added dropwise 1.1 mL (11.5 mmol) of boron tribromide over 15 minutes. The reaction was allowed to warm to room temperature and stirred for 20 hr before quenching with water (5 mL). The layers were separated and the organic layer dried (Na2SO4), filtered and evaporated. The residue was chromatographed on silica to give the title compound. 1H NMR (DMSO) δ 9.24 (1H, s), 7.79 (2H, bs), 7.70 (4H, m), 6.87 (1H, d), 6.81 (1H, d), 6.59 (1H, dd), 4.43 (1H, bs), 3.40 2.08 (1H, m), 1.77 (4H, m), 1.61 (1H, m), 1.32 (4H, m). 5H concealed by DMSO and water signals.

後処理

  1. custombefore quenching with water (5 mL)
  2. customThe layers were separated
  3. dry with materialthe organic layer dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was chromatographed on silica

出典と根拠

ORDレコード
ord-e4d6537816ac4fc1be6ed4a14f3a09b8
出典データセット
uspto-grants-2008_08
特許番号
US07414067B2

関連ノート

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