1,3-Bis(diphenylphosphino)propane → HCID 67217142, Verbindung

HRID 2068407Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2068407
C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:31]1[C:39]2[C:34](=[N:35][CH:36]=[C:37]([C:40]3[CH:41]=[C:42]([CH:50]=[CH:51][C:52]=3[CH3:53])[C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH:38]=2)[O:33][C:32]=1[C:54]1[CH:59]=[CH:58][C:57]([F:60])=[CH:56][CH:55]=1>CO.CS(C)=O.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:46]([O:45][C:43]([C:42]1[CH:50]=[CH:51][C:52]([CH3:53])=[C:40]([C:37]2[CH:38]=[C:39]3[C:31]([C:43]([O:45][CH3:46])=[O:44])=[C:32]([C:54]4[CH:55]=[CH:56][C:57]([F:60])=[CH:58][CH:59]=4)[O:33][C:34]3=[N:35][CH:36]=2)[CH:41]=1)=[O:44])([CH3:48])([CH3:49])[CH3:47]

Komponenten

7

Edukt 2

HCID 812191,3-Bis(diphenylphosphino)propaneHCID 67217138Tert-butyl 3-(3-bromo-2-(4-fluorophenyl)furo[2,3-b]pyridin-5-yl)-4-methylbenzoate

Produkt 1

HCID 67217142HCID 67217142, VerbindungAusbeute 190,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1,3-bis(diphenylphosphino)propane (119 mg, 0.287 mmol) was added to a stirring solution of palladium(II) acetate (32 mg, 0.144 mmol) and tert-butyl 3-(3-bromo-2-(4-fluorophenyl)furo[2,3-b]pyridin-5-yl)-4-methylbenzoate (231 mg, 0.479 mmol) in MeOH (1.6 mL) and DMSO (3 mL) at 80° C. in a PARR bomb which was then charged with 300 psi CO (g) and allowed to stir overnight. The mixture was diluted with EtOAc and filtered through a pad of celite. The filtrate was washed with sat. aq. NaHCO3, and brine. The organic phase was dried over Na2SO4, filtered and concentrated to give the expected product methyl 5-(5-(tert-butoxycarbonyl)-2-methylphenyl)-2-(4-fluorophenyl)furo[2,3-b]pyridine-3-carboxylate (211 mg, 0.457 mmol, 95% yield) crude by LCMS which was used directly in the next step. LC-MS retention time: 2.32 min; m/z (MH+): 462. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters XBridge 5 u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 5% MeOH/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% MeOH/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode.

Aufarbeitung

  1. additionwas then charged with 300 psi CO (g)
  2. filtrationfiltered through a pad of celite
  3. washThe filtrate was washed with sat. aq. NaHCO3, and brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6a63bff3034c4b51b6183cd062f55e60
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293909B2

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