3-Cyanophenylboronic acid → HCID 178419069, Verbindung

HRID 1760311

Reaktionsgleichung

Reaktionsgleichung von HRID 1760311
C([O:8][N:9]=[C:10]1[C:18]2([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:17]2[C:12](=[CH:13][CH:14]=[C:15](Br)[CH:16]=2)[NH:11]1)C1C=CC=CC=1.[C:25]([C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1)#[N:26]>C(#N)C1C=CC=CC=1>[C:25]([C:27]1[CH:28]=[C:29]([C:15]2[CH:16]=[C:17]3[C:12](=[CH:13][CH:14]=2)[NH:11][C:10](=[N:9][OH:8])[C:18]23[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:30]=[CH:31][CH:32]=1)#[N:26]

Komponenten

4

Edukt 2

HCID 27343253-Cyanophenylboronic acidHCID 178419047HCID 178419047, Verbindung

Produkt 1

HCID 178419069HCID 178419069, VerbindungAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7505BenzonitrileLösungsmittel

Versuchsvorschrift

3-[Spiro[cyclohexane-1,3′-[3H]indol]-(1′H)-one-2′-(O-benzyloxime)]benzonitrile [3H]indol]-5-yl]benzonitrile. Prepared from 5′-bromospiro{cyclohexane-1,3′-[3H]indol}-2′(1′H)-one 2′(O-benzyloxime) (1.0 g, 2.6 mmol) and 3-cyanophenyl boronic acid (0.76 g, 5.2 mmol) according to Example 45 procedure A. The product was purified by flash silica gel chromatography (eluant: 10:0.5 hexane:ethyl acetate) to give the desired product (0.75 g, 1.8 mmol, 71%) as a viscous oil. 1H NMR (500 MHz, DMSO-d6) δ 1.41-1.81 (8H, m), 1.96-2.03 (2H, q), 5.01 (2H, s), 6.86 (1H, d), 7.28-7.33 (9H, m), 7.95-7.97 (1H, d), 8.12 (1H, s), 9.65 (1H, s); MS (ESI(−ve)) m/z 406 (M−H)−.

Aufarbeitung

  1. customThe product was purified by flash silica gel chromatography (eluant: 10:0.5 hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a9633a0843cb4a2a9184ca4d484a8c47
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06841568B2

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