5-Indolylboronic acid → 2-(1H-Indol-5-yl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one

HRID 33329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 33329
[C:1]1([C:7]2[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[C:19](=[O:20])[NH:18][CH2:17][CH2:16][C:15]=2[C:14]=34)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:21]1C2C(=CC(B(O)O)=CC=2)[CH:23]=[CH:22]1>>[NH:21]1[C:4]2[C:5](=[CH:6][C:1]([C:7]3[NH:8][C:9]4[CH:10]=[CH:11][CH:12]=[C:13]5[C:19](=[O:20])[NH:18][CH2:17][CH2:16][C:15]=3[C:14]=45)=[CH:2][CH:3]=2)[CH:23]=[CH:22]1

Komponenten

3

Edukt 2

HCID 27343615-Indolylboronic acidHCID 102208822-Phenyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-9-one

Produkt 1

HCID 118227542-(1H-Indol-5-yl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one

Versuchsvorschrift

In a manner similar to that described for Compound 12, the tricyclic bromide (530 mg, 2.00 mmol) and indole-5-boronic acid (354 mg, 2.20 mmol) were coupled to yield 2-(1H-indol-5-yl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one, 396 mg (66%) as a beige solid: m.p. 315-317° C. (dec); 1H NMR (300 MHz, d6-DMSO) δ 3.10 (m, 2H), 3.41 (m, 2H), 6.54 (m, 1H), 7.17 (t, J=7.8 Hz, 1H), 7.42 (m, 2H), 7.55 (m, 2H), 7.68 2H), 7.68 (d, J=7.5 Hz, 1H), 7.83 (br s, 1H), 8.05 (br t, 1H), 11.26 (br s, 1H), 11.48 (br s, 1H). MS (electrospray, MH+) 302. Anal. (C19H15N3O.0.25 H2O) C, H, N.

Quellen und Nachweise

ORD-Eintrag
ord-32fc15d1e1fa4b5193e1d665ec50ce58
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429578B2

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