Triethylamine → Ethyl 6-((3-bromophenyl)amino)-5-cyclopropyl-2-(4-fluorophenyl)benzofuran-3-carboxylate

HRID 2272368Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2272368
[NH2:1][C:2]1[C:22]([CH:23]2[CH2:25][CH2:24]2)=[CH:21][C:5]2[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=3)[O:8][C:4]=2[CH:3]=1.[Br:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1.C(N(CC)CC)C>CCOC(C)=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:26][C:27]1[CH:32]=[C:31]([NH:1][C:2]2[C:22]([CH:23]3[CH2:25][CH2:24]3)=[CH:21][C:5]3[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:7]([C:9]4[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=4)[O:8][C:4]=3[CH:3]=2)[CH:30]=[CH:29][CH:28]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 2734318(3-Bromophenyl)boronic acidHCID 67353798Ethyl 6-amino-5-cyclopropyl-2-(4-fluorophenyl)benzofuran-3-carboxylate

Produkt 1

HCID 71258359Ethyl 6-((3-bromophenyl)amino)-5-cyclopropyl-2-(4-fluorophenyl)benzofuran-3-carboxylateAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of ethyl 6-amino-5-cyclopropyl-2-(4-fluorophenyl)benzofuran-3-carboxylate (1.00 g, 2.95 mmol), (3-bromophenyl)boronic acid (1.184 g, 5.89 mmol), copper(II) acetate (0.803 g, 4.42 mmol), triethylamine (1.232 mL, 8.84 mmol) and 4 A molecular sieves (2 g) was stirred at room temperature for 24 hours. The reaction mixture was diluted with EtOAc and filtered through Celite. The solvent was evaporated and the residue was purified by chromatography on silica gel (hexane:EtOAc) to give ethyl 6-((3-bromophenyl)amino)-5-cyclopropyl-2-(4-fluorophenyl)benzofuran-3-carboxylate (740 mg, 51%). LCMS (m/z, ES+)=494, 496 (M+H, M+2).

Aufarbeitung

  1. filtrationfiltered through Celite
  2. customThe solvent was evaporated
  3. customthe residue was purified by chromatography on silica gel (hexane:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-7e9bf8f60e84413a8445b41a1bf6dc39
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09119868B2

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