Water → Ethyl 6-chloro-1-(cyanomethyl)-5-methylindole-2-carboxylate

HRID 857451

반응식

HRID 857451 반응식
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8]2)=[CH:4][C:3]=1[CH3:16].[H-].[Na+].Cl[CH2:20][C:21]#[N:22].O>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:8]2[CH2:20][C:21]#[N:22])=[CH:4][C:3]=1[CH3:16]

참가 물질

6

반응물 4

HCID 962WaterHCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 21868716Ethyl 6-chloro-5-methyl-1h-indole-2-carboxylate

생성물 1

HCID 21868765Ethyl 6-chloro-1-(cyanomethyl)-5-methylindole-2-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
0 °C

실험 절차

A solution of ethyl 6-chloro-5-methylindole-2-carboxylate (1.5 g, 6.3 mmol) in DMF (30 mL) was added dropwise to a stirred suspension of sodium hydride (60%, 0.39 g, 10 mmol) in DMF (20 mL) at room temperature under Ar. The reaction was then cooled to 0° C. and stirred for 45 min then chloroacetonitrile (0.81 mL, 13 mmol) was added in one portion. The reaction was heated to 75° C. and stirred for 1 h. After allowing to cool to room temperature the mixture was poured into water (200 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine (1×100 mL), dried (magnesium sulfate), filtered and the solvent removed under vacuum to leave the crude product which was used immediately.

후처리

  1. temperatureThe reaction was heated to 75° C.
  2. stirringstirred for 1 h
  3. temperatureto cool to room temperature the mixture
  4. extractionextracted with ethyl acetate (3×100 mL)
  5. washThe combined organic extracts were washed with brine (1×100 mL)
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. customthe solvent removed under vacuum

출처 및 근거

ORD 기록
ord-f85ef82ab3724da99f2d114d364ba6a9
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07145009B2

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