1-Chloro-4-(chloromethyl)benzene → Ethyl 1-(4-chlorobenzyl)-1H-indole-2-carboxylate

HRID 967096노트

반응식

HRID 967096 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[H-].[Na+].[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1>CN(C=O)C>[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[C:2]2[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:20][CH:19]=1

참가 물질

5

반응물 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 73125Ethyl indole-2-carboxylate

생성물 1

HCID 10519288Ethyl 1-(4-chlorobenzyl)-1H-indole-2-carboxylate수율 74%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Ethyl indole-2-carboxylate (0.5 g) was dissolved in DMF and sodium hydride (0.116 g) was added in a single portion. The reaction was stirred for 1 hour, then 4-chlorobenzyl chloride (0.468 g) was added dropwise. Stirring was continued for a further 2 hours and then the reaction was quenched by the addition of water. The reaction mixture was partitioned between water and ethyl acetate. Combined organic extracts were dried (MgSO4) and concentrated in vacuo and the residue purified by column chromatography using isohexane-5% ethyl acetate as eluent to give the desired end product as a white solid (0.61 g, 74%), mp 107-108°; NMR δ (CD3SOCD3) 1.25 (t, 3H), 4.3 (q, 2H), 5.8 (s, 2H), 7.1 (t, 1H), 7.3 (m, 4H), 7.55 (d, 1H), 7.7 (d, 1H); M/z (+) 314 (MH+).

후처리

  1. stirringStirring
  2. waitwas continued for a further 2 hours
  3. customthe reaction was quenched by the addition of water
  4. customThe reaction mixture was partitioned between water and ethyl acetate
  5. dry with materialCombined organic extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customthe residue purified by column chromatography

출처 및 근거

ORD 기록
ord-14765ffbb9c848f19a4bfd895f505362
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06953809B2

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