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HRID 489536Erstellt: 24. Oktober 2026

Sodium Carbonate → 2-[3-(2-Hydroxy-ethyl)-phenyl]-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one

https://huagongshe.com/de/reaction/489536

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktSodium CarbonateHCID 10340—
EduktPotassium AcetateHCID 517044—
EduktBis(pinacolato)diboraneHCID 2733548—
Edukt2-(3-Bromophenyl)ethan-1-olHCID 2734090—
Edukt2-Bromo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-oneHCID 9943230—
KatalysatorBis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)HCID 178418228—
Produkt2-[3-(2-Hydroxy-ethyl)-phenyl]-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-oneHCID 22266709—

Reaktionsschritte

In a manner similar to that described for Example YY, 3-bromophenethyl alcohol (201 mg, 1.00 mmol), diboron pinacol ester (279 mg, 1.10 mmol), 1,1′-bis(diphenylphosphino)ferrocene dichloropalladium (24 mg, 0.03 mmol), and potassium acetate (294 mg, 3.00 mmol), 2-bromo-3,4,5,6-tetrahydro-azepino[5,4,3-cd]indol-6-one (239 mg, 0.90 mmol), a second portion of 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium (24 mg, 0.03 mmol), and sodium carbonate (2.5 mL of a 2.0 M aqueous solution, 5.00 mmol) were reacted to yield 2-[3-(2-hydroxy-ethyl)-phenyl]-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one, 135 mg (44%) as an off-white solid: m.p. 187.5-188.5° C.; 1H NMR (300 MHz, d6-DMSO) δ 2.82 (t, J=6.9 Hz, 2H), 3.12 (m, 2H), 3.39 (m, 2H), 3.69 (Abq, J=7.2, 5.1 Hz, 2H), 4.71 (t, J=5.1 Hz, 1H), 7.21 (t, J=7.8 Hz, 1H), 7.25 (d, J=7.2 Hz, 1H), 7.49 (m, 4H), 7.68 (dd, J=7.5, 0.9 Hz, 1H), 8.08 (br t, 1H), 11.55 (br s, 1H). MS (FAB, MH+): 307. Anal. (C19H18N2O2.0.1 H2O) C, H, N.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS06977298B2
Quelldatensatzuspto-grants-2005_12
ORD IDord-bb180f76afee4da9b6939cbd29dc534e
Quellennotizuspto-grants-2005_12