Tributylphosphine → 4-[3-(2,6-Dichloro-phenyl-5-isopropyl-isoxazol-4-ylmethoxy]-2-methyl-phenyl}-1H-indole-3-carboxylic acid methyl ester

HRID 250282Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 250282
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14]O)=[C:12]([CH:16]([CH3:18])[CH3:17])[O:11][N:10]=1.[CH3:19][O:20][C:21]([C:23]1[C:31]2[C:26](=[CH:27][C:28]([C:32]3[CH:37]=[CH:36][C:35](O)=[CH:34][C:33]=3[CH3:39])=[CH:29][CH:30]=2)[NH:25][CH:24]=1)=[O:22].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=[O:43].C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:19][O:20][C:21]([C:23]1[C:27]2[C:26](=[CH:31][CH:30]=[CH:29][C:28]=2[C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:43][CH:9]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=3[Cl:8])[C:13]3[CH:14]=[N:10][O:11][C:12]=3[CH:16]([CH3:18])[CH3:17])[C:33]=2[CH3:39])[NH:25][CH:24]=1)=[O:22]

Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 10850745(3-(2,6-Dichlorophenyl)-5-isopropylisoxazol-4-yl)methanolHCID 57443273HCID 57443273, Verbindung

Produkt 1

HCID 866254054-[3-(2,6-Dichloro-phenyl-5-isopropyl-isoxazol-4-ylmethoxy]-2-methyl-phenyl}-1H-indole-3-carboxylic acid methyl esterAusbeute 43,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of [3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazol-4-yl]-methanol (112 mg, 0.391 mmol) and 6-(4-hydroxy-2-methyl-phenyl)-1H-indole-3-carboxylic acid methyl ester (100 mg, 0.355 mmol) and toluene (7 mL) is added 1,1′-(azodicarbonyl)dipiperidine (99 mg, 0.39 mmol) followed by tri-n-butylphosphine (105 μL, 0.426 mmol). The mixture is allowed to stir overnight at room temperature. The reaction mixture is concentrated and purified via chromatography cluting with CH2Cl2 to give 85 mg (40%) of the title compound. ES/MS m/e 549.0 (M+1).

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated
  2. custompurified via chromatography

Quellen und Nachweise

ORD-Eintrag
ord-95146fbc922b4a7ea608e918964be6e1
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863302B2

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