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

HRID 1748252노트

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HRID 1748252 반응식
[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]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 44754779Diethyl 1H-indole-2,6-dicarboxylate2회

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-9a3a139b627f4532b5db0026244479b1
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150577B2

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