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

Participants

Role	Name	HCID	Charge
Reactant	5-Indolylboronic acid	HCID 2734361	—
Reactant	2-Phenyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-9-one	HCID 10220882	—
Product	2-(1H-Indol-5-yl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one	HCID 11822754	—

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07429578B2
Source dataset	uspto-grants-2008_09
ORD ID	ord-32fc15d1e1fa4b5193e1d665ec50ce58
Source note	uspto-grants-2008_09