N-bromobutanimide → Ethyl 3-bromo-5-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylate

HRID 1875038ノート

反応式

HRID 1875038 の反応式
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]([O:13][C:14]([NH:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20]2)=[O:15])([CH3:12])[CH3:11]>ClCCl>[Br:1][C:20]1[C:19]2[C:23](=[CH:24][CH:25]=[C:17]([NH:16][C:14]([O:13][C:10]([CH3:9])([CH3:11])[CH3:12])=[O:15])[CH:18]=2)[NH:22][C:21]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 22105416Ethyl 5-[(tert-butoxycarbonyl)amino]-1H-indole-2-carboxylate

生成物 1

HCID 68484480Ethyl 3-bromo-5-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylate収率 90.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

N-Bromosuccinimide (0.095 g, 0.536 mmol) was added to a solution of ethyl 5-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylate (0.163 g, 0.536 mmol) in dichloromethane (5 mL). The mixture was stirred at room temperature overnight. The solvent was evaporated. The residue was taken up in ethyl acetate and washed with water. The organic layer was dried over sodium sulfate and concentrated to give the title compound (0.186 g, 48%) as an off-white solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.97 (br. s., 1H), 7.70 (s, 1H), 7.28-7.39 (m, 2H), 6.54 (br. s., 1H), 4.33-4.54 (m, 2H), 1.54 (s, 9H), 1.39-1.48 (m, 3H). ES MS: m/z 381, 383.

後処理

  1. customThe solvent was evaporated
  2. washwashed with water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-7e37500eefd7420fb141a1286809050b
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

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