Potassium Carbonate → diethyl 1-(cyanomethyl)-1H-indole-2,6-dicarboxylate

HRID 1748252ノート

反応式

HRID 1748252 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]=2)[CH:3]=[C:2]1[C:15]([O:17][CH2:18][CH3:19])=[O:16].C([O-])([O-])=O.[K+].[K+].Br[CH2:27][C:28]#[N:29]>CN(C=O)C.CCOC(C)=O>[C:28]([CH2:27][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]=2)[CH:3]=[C:2]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:29]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 44754779Diethyl 1H-indole-2,6-dicarboxylate2 回

生成物 1

HCID 58767564diethyl 1-(cyanomethyl)-1H-indole-2,6-dicarboxylate収率 84.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a solution of diethyl 1H-indole-2,6-dicarboxylate (Intermediate A, 4.0 g, 15.3 mmol) in dry DMF (50 mL) is added K2CO3 (6.3 g, 45.9 mmol). The reaction mixture is stirred under N2 for 30 min. Bromoacetonitrile (2.1 mL, 30.6 mmol) is added and the reaction mixture is heated to 80° C. for 4 h. After cooling, the reaction mixture is taken up in EtOAc (300 mL) and washed with water, then brine, dried (Na2SO4) and concentrated. The residue is recrystallized from ethanol to afford the title compound (3.9 g, 84%) as fine off-white needles.

後処理

  1. temperatureAfter cooling
  2. washwashed with water
  3. dry with materialbrine, dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue is recrystallized from ethanol

出典と根拠

ORDレコード
ord-9a3a139b627f4532b5db0026244479b1
出典データセット
uspto-grants-2015_10
特許番号
US09150577B2

反応ノート

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