4-Fluorophenylboronic acid → (1S)-1-(2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}phenyl)ethanol

HRID 735316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 735316
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C@@H:21]([OH:23])[CH3:22])(=[O:14])=[O:13])[CH:6]=[CH:5]2.[F:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1>>[F:24][C:25]1[CH:30]=[CH:29][C:28]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C@@H:21]([OH:23])[CH3:22])(=[O:14])=[O:13])[CH:6]=[CH:5]3)=[CH:27][CH:26]=1

Komponenten

3

Edukt 2

HCID 2856454-Fluorophenylboronic acidHCID 68899466(1S)-1-{2-[(6-bromo-2-naphthyl)sulfonyl]phenyl}ethanol

Produkt 1

HCID 68899332(1S)-1-(2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}phenyl)ethanolAusbeute 83,5 %

Versuchsvorschrift

The title compound was prepared from (1S)-1-{2-[(6-bromo-2-naphthyl)sulfonyl]phenyl}ethanol (2.0 g, 5.1 mmol) and 4-fluorobenzeneboronic acid (1.1 g, 7.6 mmol) according to the methods of Example 2 Step 1. Crude product was first purified by flash column chromatography eluting with a 20-80% diethyl ether/isohexane gradient then a second flash column chromatography eluting with 10% diethyl ether/dichloromethane. Crystallisation from methanol/H2O gave (1S)-1-(2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}phenyl)ethanol (1.73 g, 83%). 1H NMR (500 MHz, CDCl3) δ 8.55 (1H, s), 8.17 (1H, d, J 8.0 Hz), 8.05 (1H, d, J 8.6 Hz), 8.02 (1H, s), 7.97 (1H, d, J 8.7 Hz), 7.84 (1H, dd, J 1.5, 8.5 Hz), 7.76 (2H, d, J 8.4 Hz), 7.69-7.63 (3H, m), 7.49 (1H, t, J 7.2 Hz), 7.19 (2H, t, 8.6 Hz), 5.68-5.62 (1H, m), 2.49 (1H, d, J 3.1 Hz), 1.35 (3H, d, J 6.3 Hz); m/z (ES+) 389 [(M-OH)+].

Aufarbeitung

  1. customCrude product was first purified by flash column chromatography
  2. washeluting with a 20-80% diethyl ether/isohexane
  3. washa second flash column chromatography eluting with 10% diethyl ether/dichloromethane
  4. customCrystallisation from methanol/H2O

Quellen und Nachweise

ORD-Eintrag
ord-86d42800e59141a5a9192d19832388d1
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592456B2

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