1-Cyclopropylethanol → [4-(3-cyano-1-cyclobutyl-6-hydroxy-1H-indol-2-yl)-phenyl]-carbamic acid 1-cyclopropyl-ethyl ester

HRID 252609

反応式

HRID 252609 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:20]3[CH2:23][CH2:22][CH2:21]3)[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([OH:19])[CH:11]=3)=[CH:4][CH:3]=1.Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][C:31]([N+]([O-])=O)=C[CH:29]=1)=[O:26].C1(C(C)O)CC1>N1C=CC=CC=1.Cl>[CH:33]1([CH:28]([O:27][C:25](=[O:26])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[N:9]([CH:20]4[CH2:21][CH2:22][CH2:23]4)[C:10]4[C:15]([C:16]=3[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([OH:19])[CH:11]=4)=[CH:4][CH:3]=2)[CH3:29])[CH2:32][CH2:31]1

参加物

6

反応物 3

HCID 791041-CyclopropylethanolHCID 821294-Nitrophenyl chloroformateHCID 497727192-(4-Aminophenyl)-1-cyclobutyl-6-hydroxy-indole-3-carbonitrile

生成物 1

HCID 59425704[4-(3-cyano-1-cyclobutyl-6-hydroxy-1H-indol-2-yl)-phenyl]-carbamic acid 1-cyclopropyl-ethyl ester収率 80%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 1049Pyridine溶媒

実験手順

To a solution of 2-(4-aminophenyl)-1-cyclobutyl-6-hydroxy-1H-indole-3-carbonitrile (909 mg, 3 mmol) in pyridine (5 mL) is added 4-nitrophenyl chloroformate (6 mmol) at room temperature and then stirred for 2 h at room temperature. To the reaction is added cyclopropyl methyl carbinol and then stirred for 8 h at 80° C. The reaction mixture is diluted with 1N HCl and then extracted with ethyl acetate. The organic layer is concentrated and the residue is dissolved in EtOAc and triturated with hexane. The precipitate is collected by filtration and washed with hexane and dried in vacuo to afford [4-(3-cyano-1-cyclobutyl-6-hydroxy-1H-indol-2-yl)-phenyl]-carbamic acid 1-cyclopropyl-ethyl ester (996 mg, 80%).

後処理

  1. stirringstirred for 8 h at 80° C
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layer is concentrated
  4. dissolutionthe residue is dissolved in EtOAc
  5. customtriturated with hexane
  6. filtrationThe precipitate is collected by filtration
  7. washwashed with hexane
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-d7904bb0a8d342eaa6b82260d1848e1d
出典データセット
uspto-grants-2011_01
特許番号
US07868037B2

関連ノート

読み込み中…