Triethylamine → 1-(4-Fluoro-2-methylphenyl)-2-(3-{[(4-fluorophenyl)sulfonyl]methyl}azetidin-1-yl)ethanone

HRID 10211

Reaktionsgleichung

Reaktionsgleichung von HRID 10211
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][CH:13]2[CH2:16][NH:15][CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.CCN(CC)CC.Br[CH2:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=1[CH3:35])=[O:27]>CC#N>[F:34][C:31]1[CH:32]=[CH:33][C:28]([C:26](=[O:27])[CH2:25][N:15]2[CH2:16][CH:13]([CH2:12][S:9]([C:6]3[CH:7]=[CH:8][C:3]([F:2])=[CH:4][CH:5]=3)(=[O:11])=[O:10])[CH2:14]2)=[C:29]([CH3:35])[CH:30]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 125933332-Bromo-1-(4-fluoro-2-methylphenyl)ethanoneHCID 219783933-{[(4-Fluorophenyl)sulfonyl]methyl}azetidine hydrochloride

Produkt 1

HCID 113609691-(4-Fluoro-2-methylphenyl)-2-(3-{[(4-fluorophenyl)sulfonyl]methyl}azetidin-1-yl)ethanoneAusbeute 56,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine hydrochloride (75 mg, 0.28 mmol) in MeCN (5 mL) was treated with Et3N (97 μL, 0.7 mmol) and 2-bromo-1-(4-fluoro-2-methylphenyl)ethanone (72 mg, 0.31 mmol) and stirred for 30 min at room temperature. The reaction was evaporated and the residue dissolved in DCM and purified using 10 g silica bond-elute cartridge on the personal flash master. The column was eluted with 0.5% MeOH/DCM then 1% MeOH/DCM to give the title compound as a cream solid (60 mg, 56%). 1H NMR (500 MHz, CDCl3)δ2.49 (3H, s), 2.93–2.98 (1H, m), 3.08 (2H, t, J=7.4 Hz), 3.41 (2H, d, J=7.4 Hz), 3.62 (2H, t, J=7.4 Hz), 3.77 (2H, s), 6.89–6.95 (2H, m), 7.23–7.27 (2H, t, J=8.8 Hz), 7.61 (1H, dd, J=5.8 & 8.5 Hz), 7.90–7.92 (2H, dd, J=5.2 & 8.8 Hz). m/z (ES+) 380 (M+H)+.

Aufarbeitung

  1. customThe reaction was evaporated
  2. dissolutionthe residue dissolved in DCM
  3. custompurified
  4. washbond-elute cartridge on the personal flash master
  5. washThe column was eluted with 0.5% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-90d80e2f9bb54732b7ab62b6b89fce5e
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094777B2

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