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N,N'-Dimethylethylenediamine → 5-(4-tert-Butylphenyl)-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester

HRID 646094
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HRID 646094 반응식
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[O-]P([O-])([O-])=O.[K+].[K+].[K+].CNCCNC.Br[C:40]1[CH:45]=[CH:44][C:43]([O:46][CH:47]([CH3:49])[CH3:48])=[CH:42][CH:41]=1>C1(C)C=CC=CC=1.CCOC(C)=O.[Cu]I>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:40]2[CH:45]=[CH:44][C:43]([O:46][CH:47]([CH3:49])[CH3:48])=[CH:42][CH:41]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]1[CH:16]=[CH:17][C:18]([C:21]([CH3:23])([CH3:22])[CH3:24])=[CH:19][CH:20]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]
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참가 물질

8

반응물 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 2280881-Bromo-4-(propan-2-yloxy)benzeneHCID 68475095Ethyl 5-(4-(tert-butyl)phenyl)-1H-indole-2-carboxylate

생성물 1

HCID 687003415-(4-tert-Butylphenyl)-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester수율 95.1%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

5-(4-tert-Butylphenyl)indole-2-carboxylic acid ethyl ester (198 mg, 0.60 mmol; see step (a) above), CuI (12 mg, 0.06 mmol), K3PO4 (254 mg, 1.2 mmol), N,N′-dimethyl-1,2-diaminoethane (20 μL, 0.18 mmol) and 1-bromo-4-isopropoxybenzene (258 mg, 1.2 mmol) in toluene (2 mL) was heated at 110° C. for 17 h. The mixture was diluted with EtOAc and washed with NaHCO3 (aq. sat.), HCl (aq. 0.1 M), brine and then dried over Na2SO4. Concentration and purification by chromatography gave the sub-title compound (260 mg, 94%).

후처리

  1. washwashed with NaHCO3 (aq. sat.), HCl (aq. 0.1 M), brine
  2. dry with materialdried over Na2SO4
  3. concentrationConcentration and purification by chromatography

출처 및 근거

ORD 기록
ord-e2863fda51484e9780a671f7933b8df4
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07705023B2

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