Cesium fluoride → [4-(2-Azepan-1-yl-ethoxy)-phenyl]-[6-methoxy-2-(2,3,5-trifluorophenyl)-naphthalen-1-yl]-methanone

HRID 1513968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1513968
[N:1]1([CH2:8][CH2:9][O:10][C:11]2[CH:38]=[CH:37][C:14]([C:15]([C:17]3[C:26]4[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=4)[CH:20]=[CH:19][C:18]=3OS(C(F)(F)F)(=O)=O)=[O:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F-].[Cs+].Br[C:42]1[CH:47]=[C:46]([F:48])[CH:45]=[C:44]([F:49])[C:43]=1[F:50]>C(#N)C.[Pd].C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.[Pd]>[N:1]1([CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([C:17]3[C:26]4[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=4)[CH:20]=[CH:19][C:18]=3[C:42]3[CH:47]=[C:46]([F:48])[CH:45]=[C:44]([F:49])[C:43]=3[F:50])=[O:16])=[CH:37][CH:38]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Komponenten

7

Edukt 3

HCID 25953Cesium fluorideHCID 27363991-Bromo-2,3,5-trifluorobenzeneHCID 57552509Trifluoromethanesulfonic acid 1-[4-(2-azepan-1-yl-ethoxy)-benzoyl]-6-methoxynaphthalen-2-yl ester

Produkt 1

HCID 57552540[4-(2-Azepan-1-yl-ethoxy)-phenyl]-[6-methoxy-2-(2,3,5-trifluorophenyl)-naphthalen-1-yl]-methanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 2734559Bis(tricyclohexylphosphine) palladium(0)KatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Dissolve trifluoromethanesulfonic acid 1-[4-(2-azepan-1-yl-ethoxy)-benzoyl]-6-methoxynaphthalen-2-yl ester (2.60 g, 6.53 mmol) in 200 mL acetonitrile and add to this bis(pinacoloato)diboron (1.5 g, 7.96 mmol), bis(tricyclohexylphosphine)palladium (0) (0.72 g, 1.50 mmol) and cesium fluoride (7.33 g, 67.0 mmol). Heat the reaction to 100° C. until LC/MS indicates all starting material is consumed. Add to this mixture 1-bromo-2,3,5-trifluorobenzene (2.00 g, 13.06 mmol) and another 720 mg of palladium catalyst and heat at 80° C. for 24 hours. Filter the reaction, concentrate filtrate and purify on a silica gel column eluting with a 0-10% methanol/methylene chloride gradient. The yield is 1.85 g (53%)

Aufarbeitung

  1. temperatureHeat
  2. customthe reaction to 100° C. until LC/MS
  3. customis consumed
  4. filtrationFilter
  5. customthe reaction
  6. concentrationconcentrate filtrate
  7. custompurify on a silica gel column
  8. washeluting with a 0-10% methanol/methylene chloride gradient

Quellen und Nachweise

ORD-Eintrag
ord-99f37703d60e4d299ea6b20b3488e082
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217032B2

Notizen zur Reaktion

Wird geladen…