Sodium Carbonate → 5-[3,5-Bis(trifluoromethyl)phenyl]-3-{[2'-methoxy-4,5'-bis(trifluoromethyl)-biphenyl-2-yl]methyl}-1,3-oxazolidin-2-one

HRID 1028638

Reaktionsgleichung

Reaktionsgleichung von HRID 1028638
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3I)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:33][O:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][C:36]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[C:36]3[CH:37]=[C:38]([C:41]([F:44])([F:43])[F:42])[CH:39]=[CH:40][C:35]=3[O:34][CH3:33])[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 27826762-Methoxy-5-(trifluoromethyl)phenylboronic acidHCID 591352395-[3,5-Bis(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]1,3-oxazolidin-2-one

Produkt 1

HCID 591350765-[3,5-Bis(trifluoromethyl)phenyl]-3-{[2'-methoxy-4,5'-bis(trifluoromethyl)-biphenyl-2-yl]methyl}-1,3-oxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397HCID 178418397, VerbindungKatalysator

Versuchsvorschrift

5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]-1,3-oxazolidin-2-one (Example 66, 100 mg; 0.171 mmol) was treated with [2-methoxy-5-(trifluoromethyl)phenyl]boronic acid (Step B, 113 mg; 0.514 mmol), tetrakis(triphenylphosphine)palladium (0) (24 mg; 0.0206 mmol), and sodium carbonate (148 mg) as described in Example 291 to afford 5-[3,5-bis(trifluoromethyl)phenyl]-3-{[2′-methoxy-4,5′-bis(trifluoromethyl)-biphenyl-2-yl]methyl}-1,3-oxazolidin-2-one as a clear glass. LCMS=612.1 (M−19)+. 1H NMR (benzene-d6, 500 MHz, mixture of atropisomers): δ 7.61 (s, 1H), 7.40-7.36 (m, 1 H), 7.31 (s, 1 H), 7.27-7.23 (m, 4 H), 6.74-6.72 (m, 1 H), 6.35 (d, J=8.7 Hz, 1 H), 4.42-4.32 (m, 2 H), 3.70 (d, J=15.8 Hz, 1 H), 3.14 (s, 3 H), 2.28 (t, J=8.7 Hz, 1 H), 1.98 (t, J=8.2 Hz, 1 H).

Quellen und Nachweise

ORD-Eintrag
ord-8fb32cfb314845e1a9966640351db2e1
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735435B2

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