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Potassium Phosphate, Tribasic → 5-(4-Chlorophenyl)-1-(4-isopropoxyphenyl)-1H-indole-2-carboxylic acid ethyl ester

HRID 646167
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HRID 646167 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=2)[C:8]2[C:13]([C:14]=1Cl)=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C2C=CC=CC=2)C=CC=CC=1P(C(C)(C)C)C(C)(C)C.[Cl:56][C:57]1[CH:62]=[CH:61][C:60](B(O)O)=[CH:59][CH:58]=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:60]1[CH:61]=[CH:62][C:57]([Cl:56])=[CH:58][CH:59]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 742994-Chlorophenylboronic acidHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 686966545-Bromo-3-chloro-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester2회

생성물 1

HCID 687014075-(4-Chlorophenyl)-1-(4-isopropoxyphenyl)-1H-indole-2-carboxylic acid ethyl ester수율 35%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

실험 절차

A mixture of 5-bromo-3-chloro-1-(4-isopropoxyphenyl)-1H-indole-2-carboxylic acid ethyl ester (see Example 35(b) 402 mg, 1.0 mmol), K3PO4 (716 mg, 3.37 mmol), Pd(OAc)2 (22 mg, 0.1 mmol) and biphenyl-2-yldi-tert-butylphosphine (53 mg, 0.18 mmol) in toluene (10 mL) was stirred at ambient temperature for 10 min after which 4-chlorophenyl boronic acid (233 mg, 1.49 mmol) was added. The reaction was heated at reflux for 5 h, cooled to room temperature and filtered. The filter cake was washed with toluene (5 mL), the combined filtrates were concentrated and the residue was purified by chromatography to afford the sub-title compound (150 mg, 35%).

후처리

  1. additionwas added
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 5 h
  4. filtrationfiltered
  5. washThe filter cake was washed with toluene (5 mL)
  6. concentrationthe combined filtrates were concentrated
  7. customthe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-bf86c61d7e194cfc9fbf10ecc9d91c7a
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07705023B2

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