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 | 4-(8-Fluoro-3,4,5,6-tetrahydro-6-oxo-1H-pyrrolo(4,3,2-ef)(2)benzazepin-2-yl)benzaldehyde | HCID 22266721 | — |
| Reactant | 2-Bromo-8-fluoro-fluoro-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one | HCID 69276722 | — |
| Product | Indol-6-one | HCID 17925780 | — |
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-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-azepinop5,4,3-cd]indol-6-one, 16 mg (14%) as a yellow solid: m.p. 264-265° C. (dec), 1H NMR (300 MHz, d6-DMSO) δ 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), 8.25 (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 | US07429578B2 |
|---|
| Source dataset | uspto-grants-2008_09 |
|---|
| ORD ID | ord-b56498e2b2fc4286a0b0e54e2b447550 |
|---|
| Source note | uspto-grants-2008_09 |
|---|
