Potassium Carbonate → [2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-[5-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2-fluoro-phenyl]-methanone

HRID 1012657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1012657
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])[CH:5]=[CH:4][C:3]=1[C:17]([C:19]1[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:20]=1[F:26])=[O:18].[CH3:27][C:28]1([CH3:45])[O:32][CH:31]([CH2:33]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:30][O:29]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])[CH:5]=[CH:4][C:3]=1[C:17]([C:19]1[CH:24]=[C:23]([O:25][CH2:33][CH:31]2[CH2:30][O:29][C:28]([CH3:45])([CH3:27])[O:32]2)[CH:22]=[CH:21][C:20]=1[F:26])=[O:18]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2350972,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonateHCID 67314403[2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-(2-fluoro-5-hydroxy-phenyl)-methanone

Produkt 1

HCID 58677666[2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-[5-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2-fluoro-phenyl]-methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Compound 512 (54 mg, 0.14 mmol) was dissolved in acetonitrile (4 mL) in a reaction vial. Compound 506 (61 mg, 0.21 mmol) and K2CO3 (30 mg, 0.21 mmol) were added. The reaction vial was flushed with argon, closed and then stirred at 110° C. for 50 min. in a microwave oven, followed by reflux in a oil bath for 24 h. The reaction mixture was concentrated in vacuo and purified by continuously gradient flash chromatography using EtOAc/petroleum ether (40-60)(v:v=1:7 to 1:3) as the eluent, affording the title compound as a yellow oil. 13C NMR (CDCl3) δ 190.6, 159.1 (dd), 154.7, 154.5 (d), 154.4 (dd), 147.8, 134.7, 132.9, 129.6, 127.9 (d), 124.4 (dd), 124.2 (dd), 120.6 (d), 117.1 (d), 116.0, 115.1 (d), 112.9, 111.6 (dd), 109.9, 104.9 (dd), 73.9, 69.6, 66.6, 26.8, 25.4

Aufarbeitung

  1. customThe reaction
  2. customvial was flushed with argon
  3. customclosed
  4. temperatureby reflux in a oil bath for 24 h
  5. concentrationThe reaction mixture was concentrated in vacuo
  6. custompurified by continuously gradient flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-12f34305a473467c8ee22c6a50ecf568
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977387B2

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