Ethanol → Methyl 6-(4'-pentylbiphenyl-4-yl)-2-phenyl-2-(4-pyrrolidinophenyl)-2h-naphtho[1,2-b]pyran-5-carboxylate

HRID 2369643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2369643
FC(F)(F)S(O[C:7]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:10]2OC[C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[CH:14]=[C:9]2[C:8]=1C(OC)=O)(=O)=O.[CH2:44]([C:49]1[CH:54]=[CH:53][C:52]([C:55]2[CH:60]=[CH:59][C:58](B(O)O)=[CH:57][CH:56]=2)=[CH:51][CH:50]=1)[CH2:45][CH2:46][CH2:47][CH3:48].[C:64]([O-])([O-])=[O:65].[K+].[K+].[OH2:70].[CH3:71][CH2:72][OH:73]>C1(C)C=CC=CC=1.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>[CH2:44]([C:49]1[CH:54]=[CH:53][C:52]([C:55]2[CH:60]=[CH:59][C:58]([C:10]3[C:32]4[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:7]4[O:70][C:13]([C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=5)([C:15]5[CH:16]=[CH:17][C:18]([N:21]6[CH2:25][CH2:24][CH2:23][CH2:22]6)=[CH:19][CH:20]=5)[CH:14]=[CH:9][C:8]=4[C:71]=3[C:72]([O:65][CH3:64])=[O:73])=[CH:57][CH:56]=2)=[CH:51][CH:50]=1)[CH2:45][CH2:46][CH2:47][CH3:48]

Komponenten

8

Edukt 5

HCID 702EthanolHCID 962WaterHCID 11430Potassium CarbonateHCID 154580894'-Pentyl-4-biphenylboronic Acid (contains varying amounts of Anhydride)HCID 866536106-trifluoromethanesulfonyloxy-5-methoxycarbonyl-3-phenyl-3-(4-pyrrolidinophenyl)-2H-naphtho[1,2-b]pyran

Produkt 1

HCID 58274176Methyl 6-(4'-pentylbiphenyl-4-yl)-2-phenyl-2-(4-pyrrolidinophenyl)-2h-naphtho[1,2-b]pyran-5-carboxylateAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 6-trifluoromethanesulfonyloxy-5-methoxycarbonyl-3-phenyl-3-(4-pyrrolidinophenyl)-2H-naphtho[1,2-b]pyran (0.96 g, 1.6 mmol), 4′-pentyl-4-biphenylboronic acid (0.66 g, 2.5 mmol), K2CO3 (0.68 g, 49 mmol) and Pd(PPh3)4 (91 mg, 3 mol %) in PhMe (30 mL) and EtOH (30 mL) was heated at reflux for 2 h. The resulting solution was cooled, poured into water (100 mL), extracted with DCM (4×50 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was chromatographed twice on silica using PhMe (80% in hexanes). The solvent was removed under reduced pressure and the residue crystallized from acetone-MeOH to give the title compound (0.36 g, 32%) as a purple powder.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperatureThe resulting solution was cooled
  4. extractionextracted with DCM (4×50 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed under reduced pressure
  7. customThe residue was chromatographed twice on silica
  8. customThe solvent was removed under reduced pressure
  9. customthe residue crystallized from acetone-MeOH

Quellen und Nachweise

ORD-Eintrag
ord-ff0765d7a8ad4841bae77383467d0fe9
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703978B2

Notizen zur Reaktion

Wird geladen…