Potassium Carbonate → Methyl 5-(benzyloxy)-2-(4-fluorophenyl)furo[2,3-c]pyridine-3-carboxylate

HRID 44064

Reaktionsgleichung

Reaktionsgleichung von HRID 44064
[C:1]([O-])(=O)C.[Na+].[C:6]([O-:9])([O-])=[O:7].[K+].[K+].[CH2:12]([O:19][C:20]1[N:25]=[CH:24][C:23]([OH:26])=[C:22]([C:27]#[C:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO.O.O.[Cu](Cl)Cl.[Pd](Cl)Cl>[CH2:12]([O:19][C:20]1[CH:21]=[C:22]2[C:27]([C:6]([O:9][CH3:1])=[O:7])=[C:28]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[O:26][C:23]2=[CH:24][N:25]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 517045Sodium AcetateHCID 672172956-(Benzyloxy)-4-((4-fluorophenyl)ethynyl)pyridin-3-ol

Produkt 1

HCID 67217578Methyl 5-(benzyloxy)-2-(4-fluorophenyl)furo[2,3-c]pyridine-3-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24290Palladium ChlorideKatalysatorHCID 61482Cupric chloride dihydrateKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium acetate (1.14 g, 13.9 mmol), K2CO3 (1.92 g, 13.9 mmol), copper (II) chloride dihydrate (3.56 g, 20.9 mmol), palladium (II) chloride (0.205 g, 1.15 mmol) was added to a stirring solution of 6-(benzyloxy)-4-((4-fluorophenyl)ethynyl)pyridin-3-ol (2.22 g, 6.95 mmol) in MeOH (150 mL) at room temperature in a Parr Bomb. The vessel was charged with 300 PSI of CO (g) and allowed to stir at room temperature overnight. The mixture was concentrated then diluted with EtOAc and washed with H2O, and sat NaCl. The organic phase was dried over Na2SO4, filtered and concentrated to give the expected product methyl 5-(benzyloxy)-2-(4-fluorophenyl)furo[2,3-c]pyridine-3-carboxylate (2.62 g, 6.95 mmol, 100% yield) by LCMS. LC-MS retention time: 2.66 min; m/z (MH+): 378. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters SunFire 5u 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 10% acetonitrile/90% H2O/0.1% trifluoroacetic acid and solvent B was 10% H2O/90% acetonitrile/0.1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode.

Aufarbeitung

  1. additionThe vessel was charged with 300 PSI of CO (g)
  2. concentrationThe mixture was concentrated
  3. additionthen diluted with EtOAc
  4. washwashed with H2O
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-60d69960a9454e7595851349abf117d3
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536338B2

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