Pyridine → 1-cyclobutyl-6-ethoxy-2-[4-(2-pyridin-2-yl-ethylamino)-phenyl]-1H-indole-3-carbonitrile

HRID 502265

反応式

HRID 502265 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:22]3[CH2:25][CH2:24][CH2:23]3)[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=3)=[CH:4][CH:3]=1.ClC(O[C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-])=O)=[CH:32][CH:31]=1)=O.N1C=CC=C[CH:40]=1.COCCOCCO>C(Cl)Cl.ClCCCl>[CH:22]1([N:9]2[C:10]3[C:15](=[CH:14][CH:13]=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=3)[C:16]([C:17]#[N:18])=[C:8]2[C:5]2[CH:4]=[CH:3][C:2]([NH:1][CH2:31][CH2:32][C:33]3[CH:34]=[CH:35][CH:30]=[CH:40][N:36]=3)=[CH:7][CH:6]=2)[CH2:23][CH2:24][CH2:25]1

参加物

7

反応物 4

HCID 1049PyridineHCID 8134Diethylene Glycol Monomethyl EtherHCID 821294-Nitrophenyl chloroformateHCID 250520112-(4-Aminophenyl)-1-cyclobutyl-6-ethoxy-indole-3-carbonitrile

生成物 1

HCID 249582441-cyclobutyl-6-ethoxy-2-[4-(2-pyridin-2-yl-ethylamino)-phenyl]-1H-indole-3-carbonitrile収率 43.9%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

実験手順

2-(4-Aminophenyl)-1-cyclobutyl-6-ethoxy-1H-indole-3-carbonitrile (40 mg, 0.12 mmol), prepared as in example 1CM, step B, is combined with 4-nitrophenyl chloroformate (60 mg, 0.30 mmol), DCE (0.4 mL), and pyridine (25 μL, 0.31 mmol). This suspension is stirred at room temperature for 1 h. 2-(2-methoxyethoxy)ethanol (150 μL, 1.25 mmol) is added. This mixture is heated at 75° C. overnight. The reaction mixture is then diluted in CH2Cl2 and is washed with dilute aqueous NaOH to remove the yellow nitrophenol by-product. The organic layer is dried and concentrated. Purification by silica gel chromatography (CH2Cl2/EtOAc, 4/1), followed by trituration with hexanes/acetone (2/1) yields 1-cyclobutyl-6-ethoxy-2-[4-(2-pyridin-2-yl-ethylamino)-phenyl]-1H-indole-3-carbonitrile (23 mg, 42%) as a white solid.

後処理

  1. temperatureThis mixture is heated at 75° C. overnight
  2. washis washed with dilute aqueous NaOH
  3. customto remove the yellow nitrophenol by-product
  4. customThe organic layer is dried
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (CH2Cl2/EtOAc, 4/1)

出典と根拠

ORDレコード
ord-7d7234b7c6b7465d9eb80807ae4b1842
出典データセット
uspto-grants-2010_08
特許番号
US07772271B2

関連ノート

読み込み中…