2-Bromo-1-(4-fluorophenyl)ethan-1-one → HCID 21978430, Verbindung

HRID 10215

Reaktionsgleichung

Reaktionsgleichung von HRID 10215
Cl.[NH:2]1[CH2:5][CH:4]([CH2:6][S:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:3]1.Br[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)=[O:21]>>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C:20](=[O:21])[CH2:19][N:2]2[CH2:5][CH:4]([CH2:6][S:7]([C:10]3[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=3)(=[O:9])=[O:8])[CH2:3]2)=[CH:23][CH:24]=1

Komponenten

3

Edukt 2

HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 21978414HCID 21978414, Verbindung

Produkt 1

HCID 21978430HCID 21978430, VerbindungAusbeute 29 %

Versuchsvorschrift

Following the procedure of Example 2, 4-[(azetidin-3-ylmethyl)sulfonyl]benzonitrile hydrochloride (75 mg, 0.27 mmol) was reacted with 2-bromo-1-(4-fluorophenyl)ethanone. Crude product was purified on a 10 g bond elute silica cartridge using the personal flash master eluting with 0.5% MeOH/DCM to 2% MeOH/DCM to give the freebase as a pale yellow gum (30 mg, 29%). The freebase was dissolved in 3:1 ether/MeOH (5 ml) and 1.0M hydrogen chloride in ether (89μl) was added. The side of the flask was etched and the salt precipitated and was isolated by filtration and dried under vacuum to give the title compound as a white solid (20 mg). 1H NMR (500 MHz, CDCl3) δ 3.05–3.13 (1H, m), 3.90–3.96 (2H, m), 4.03–4.12 (2H, m), 4.23–4.30 (2H, m), 5.06 (2H, s), 7.44 (2H, t, J=8.8 Hz), 8.01 (2H, dd, J=5.4 & 8.8 Hz), 8.09 (2H, d, J=8.6 Hz), 8.21 (2H, d, J=8.6 Hz), 10.62 (1H, s). m/z (ES+) 373 (M+H)+.

Aufarbeitung

  1. customCrude product was purified on a 10 g bond
  2. washelute silica cartridge
  3. washeluting with 0.5% MeOH/DCM to 2% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-945dc99b109345e4a9e046f358d68973
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094777B2

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