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

Participants

Role	Name	HCID	Charge
Reactant	4-Fluorophenylboronic acid	HCID 285645	—
Reactant	2-Phenyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-9-one	HCID 10220882	—
Product	2-(4-fluorophenyl)-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one	HCID 9970889	—

Reaction Steps

In a manner similar to that described for Compound 12, the tricyclic bromide (100 mg, 0.54 mmol) and 4-fluorobenzeneboronic acid (79 mg, 0.57 mmol) were coupled to yield 2-(4-fluorophenyl)-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one, 107 mg (99%), as a pale-yellow solid. 1H NMR (300 MHz, d6-DMSO) δ 3.04 (m, 2H), 3.38 (m, 2H), 7.22 (app t, 1H, J=7.7 Hz), 7.39 (m, 2H), 7.56 (dd, 1H, J=8.0, 0.9 Hz), 7.64 (m, 3H), 8.05 (br t, 1H), 11.57 (br s, 1H); HRMS (FAB, MH+) Calcd for C17H14FN2O: 281.1090, Found: 281.1093; Anal. (C17H13FN2O.0.6 H2O) C, H, N.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06977298B2
Source dataset	uspto-grants-2005_12
ORD ID	ord-1e9d30d2be044b89b87e983a97e4a2b3
Source note	uspto-grants-2005_12