Pyrrolidine → 8-Fluoro-2-(4-pyrrolidin-1-ylmethyl-phenyl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one

Participants

Role	Name	HCID	Charge
Reactant	Pyrrolidine	HCID 31268	—
Reactant	4-Formylphenylboronic Acid	HCID 591073	—
Reactant	2-Phenyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-9-one	HCID 10220882	—
Reactant	2-Bromo-8-fluoro-4,5-dihydro-1H-azepino[5,4,3-CD]indol-6(3H)-one	HCID 22266717	—
Reactant	4-(8-Fluoro-3,4,5,6-tetrahydro-6-oxo-1H-pyrrolo(4,3,2-ef)(2)benzazepin-2-yl)benzaldehyde	HCID 22266721	—
Product	8-Fluoro-2-(4-pyrrolidin-1-ylmethyl-phenyl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one	HCID 22266715	—

Reaction Steps

In a manner similar to that described for Compound PPP, 4-(8-fluoro-6-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-2-yl) benzaldehyde (100 mg, 0.32 mmol; prepared in a manner similar to that described for compound 12 from 2-bromo-8-fluoro-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one and 4-formylphenylboronic acid) was reacted with pyrrolidine (115 mg, 1.62 mmol) to yield 8-fluoro-2-(4-pyrrolidin-1-ylmethyl-phenyl)-1,3,4,5-tetrahydro-azepino[5,4,3 -cd]indol-6-one, 16 mg (14%) as a yellow solid: m.p. 264-265° C. (dec), 1H NMR (300 MHz, d6-DMSO) 1.72 (m, 4H), 2.49 (m, 4H), 3.04 (m, 2H), 3.39 (m, 2H), 3.64 (br s, 2H), 7.31 (dd, J=9.3, 2.4 Hz, 1H), 7.43 (m, 3H), 7.58 (d, J=8.1 Hz, 2H), 8.2 (br t, 1H), 11.66 (br s, 1H). HRMS (MALDI MH+) Calcd for C22H22N3OF: 362.1825. Found: 364.1810. Anal. (C22H22N3OF.0.5 H2O) C, H, N.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06495541B1
Source dataset	uspto-grants-2002_12
ORD ID	ord-2ce5f53e0aca4737afd950d0686fcfa3
Source note	uspto-grants-2002_12