Triphenylphosphine → HCID 59497231, Verbindung

HRID 1747472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1747472
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([CH2:18]O)[CH:13]=[C:14]([Cl:17])[CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:20][O:21][C:22](=[O:35])[CH2:23][CH2:24][N:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[NH:27][C:26]1=[O:34].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([CH2:18][N:27]3[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[N:25]([CH2:24][CH2:23][C:22]([O:21][CH3:20])=[O:35])[C:26]3=[O:34])[CH:13]=[C:14]([Cl:17])[CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 594973521,1-Dimethylethyl 6-chloro-4-(hydroxymethyl)-1H-indole-1-carboxylateHCID 59497358HCID 59497358, Verbindung

Produkt 1

HCID 59497231HCID 59497231, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

6-Chloro-4-hydroxymethyl-indole-1-carboxylic acid tert-butyl ester 350 mg, 1.24 mmol and 3-(2-Oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid methyl ester (300 mg 1.36 mmol, from Example 2) are dissolved in tetrahydrofuran 6.0 mL and triphenylphospine (630 mg 1.37 mmol) is added in one portion to the reaction. The reaction is cooled to 0° C. and then diisopropyl azodicarboxylate (265 μL 1.37 mmol) is added drop wise to the reaction over 5 minutes, and warmed to room temperature. The reaction is stirred for 15 minutes and then evaporated in vacuo, and purified on silica gel with hexanes ethyl acetate as the eluent to give the title compound (280 mg, 0.58 mmol, 47%). LCMS (ESMS): m/z 484.9 (M+H+).

Aufarbeitung

  1. customwise to the reaction over 5 minutes
  2. temperaturewarmed to room temperature
  3. customevaporated in vacuo
  4. custompurified on silica gel with hexanes ethyl acetate as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-3f5699ac2e42457589dbc6001c9c3179
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150556B2

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