Cesium fluoride → 1-(4-(2-(Piperidin-1-yl)ethoxy)phenoxy)-2-(4-cyclopropanesulfonylphenyl)-6-methoxy-naphthalene

HRID 748971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 748971
[CH:1]1(S(C2C=CC(B3OC(C)(C)C(C)(C)O3)=CC=2)(=O)=O)C[CH2:2]1.[CH2:22]([O:29][C:30]1[CH:31]=[CH:32][C:33]2[C:37]([O:38][C:39]3[CH:53]=[CH:52][C:42]([O:43][CH2:44][CH2:45][N:46]4[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]4)=[CH:41][CH:40]=3)=[C:36]([C:54]3[CH:59]=[CH:58][C:57]([S:60]([CH3:63])(=[O:62])=[O:61])=[C:56](F)[CH:55]=3)S[C:34]=2[CH:65]=1)C1C=CC=CC=1.[F-].[Cs+].[CH:68]1(P(C2CCCCC2)C2CCCCC2)CCCC[CH2:69]1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[N:46]1([CH2:45][CH2:44][O:43][C:42]2[CH:41]=[CH:40][C:39]([O:38][C:37]3[C:33]4[C:34](=[CH:65][C:30]([O:29][CH3:22])=[CH:31][CH:32]=4)[CH:2]=[CH:1][C:36]=3[C:54]3[CH:55]=[CH:56][C:57]([S:60]([CH:63]4[CH2:69][CH2:68]4)(=[O:62])=[O:61])=[CH:58][CH:59]=3)=[CH:53][CH:52]=2)[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1

Komponenten

7

Edukt 4

HCID 25953Cesium fluorideHCID 75806TricyclohexylphosphineHCID 59751449(2-{4-[6-Benzyloxy-2-(3-fluoro-4-methanesulfonyl-phenyl)-benzo[b]thiophen-3-yloxy]-phenoxy}-ethyl)-piperidineHCID 685156112-(4-(Cyclopropylsulfonyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 104377421-(4-(2-(Piperidin-1-yl)ethoxy)phenoxy)-2-(4-cyclopropanesulfonylphenyl)-6-methoxy-naphthaleneAusbeute 512,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Combine 2-(4-cyclopropanesulfonyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (200 mg, 0.65 mmol), the compound of Preparation 1 (150 mg, 0.28 mmol) and cesium fluoride (214 mg, 1.4 mmol) in dried flask fitted with a reflux condenser. In a separate flask combine palladium (II) acetate (6.2 mg, 0.028 mmol) and tricyclohexylphosphine (11.7 mg, 0.042 mmol). Add acetonitrile (3.0 mL) and sonicate for 10 minutes under nitrogen. Add the catalyst solution to the solids and heat in an 80° C. oil bath for 20 minutes. Cool the suspension to room temperature and filter through packed celite. Rinse the celite with acetonitrile and evaporate. Chromatograph the residue on a SiO2 column eluting the material with methanol in dichloromethane (0 to 5%) to give 120 mg of the title compound (77%). Mass spectrum (ion spray): m/z 558.3 (M+H).

Aufarbeitung

  1. customfitted with a reflux condenser
  2. customIn a separate flask combine
  3. additionAdd the catalyst solution to the solids
  4. temperatureCool the suspension to room temperature
  5. filtrationfilter
  6. washRinse the celite with acetonitrile
  7. customevaporate
  8. washChromatograph the residue on a SiO2 column eluting the material with methanol in dichloromethane (0 to 5%)

Quellen und Nachweise

ORD-Eintrag
ord-a3e1800a15014171b4e0f83c84520682
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399867B2

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