2-Chlorophenylboronic acid → 2-(2-Chlorophenyl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one

Participants

Role	Name	HCID	Charge
Reactant	2-Chlorophenylboronic acid	HCID 2734322	—
Reactant	2-Phenyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-9-one	HCID 10220882	—
Product	2-(2-Chlorophenyl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one	HCID 9948137	—

Reaction Steps

In a manner similar to that described for Compound 12, the tricyclic bromide (210 mg, 0.79 mmol) and 2-chlorophenylboronic acid (136 mg, 0.87 mmol) were coupled to yield 2-(2-chlorophenyl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one, 78 mg (33%), as a shiny white solid. mp 275° C. (dec); 1H NMR (300 MHz, d6-DMSO) δ 2.76 (m, 2H), 3.38 (m, 2H), 7.23 (app t, 1H, J=7.8 Hz), 7.56 (m, 5H), 7.71 (dd, 1H, J=7.5, 0.9 Hz), 8.07 (br t, 1H), 11.53 (br s, 1H); MS (FAB, MH+) 297; Anal. (C17H13N2OCl.0.15 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-e6f5fa3698914cffb23a1cfcd03e0214
Source note	uspto-grants-2008_09