Triethylamine → HCID 59272982, Verbindung

HRID 2423062Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2423062
[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[N:12][NH:13]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:24]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(CC)CC)C.B(O)O>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:18][C:19]1[CH:20]=[C:21]([N:13]2[C:14]3[C:10](=[C:9]([O:8][CH2:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:17]=[CH:16][CH:15]=3)[CH:11]=[N:12]2)[CH:22]=[CH:23][C:24]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

7

Edukt 4

HCID 8471Triethylamine2×HCID 61668Boronic AcidHCID 27377884-Benzyloxy-3-fluorophenylboronic AcidHCID 231344734-(Benzyloxy)-1h-indazole

Produkt 1

HCID 59272982HCID 59272982, VerbindungAusbeute 30,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysator2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 4-[(phenylmethyl)oxy]-1H-indazole (D1) (530 mg, 2.37 mmol), {3-fluoro-4-[(phenylmethyl)oxy]phenyl}boronic acid (873 mg, 3.55 mmol), copper acetate (861 mg, 4.74 mmol), triethylamine (0.660 mL, 4.74 mmol) and powdered 4A molecular sieves (2.5 g) in dichloromethane (10 mL) was stirred vigorously under an air atmosphere at ambient temperature. Further quantities of boronic acid, triethylamine and copper acetate were added after 18 hours (0.5 equivalents of each) and 22 hours (1 equivalent of each). After stirring for a further 24 hrs, the mixture was filtered through a plug of silica gel and concentrated. Chromatography (silica gel, elution with 0-20% ethyl acetate in hexane) gave the title compound (D2) as a white solid (309 mg).

Aufarbeitung

  1. stirringAfter stirring for a further 24 hrs
  2. filtrationthe mixture was filtered through a plug of silica gel
  3. concentrationconcentrated
  4. washChromatography (silica gel, elution with 0-20% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-6b9656afa3724e89bb8e816a63f40ed1
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960563B2

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