Water → HCID 57706531, Verbindung

HRID 1662493Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662493
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1B1OC(C)(C)C(C)(C)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.O.FC(F)(F)S(O[C:73]1[CH2:78][C:77]([CH3:80])([CH3:79])[CH2:76][C:75]([CH3:82])([CH3:81])[CH:74]=1)(=O)=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[C:73]1[CH2:78][C:77]([CH3:80])([CH3:79])[CH2:76][C:75]([CH3:82])([CH3:81])[CH:74]=1

Komponenten

8

Edukt 5

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 110873803,3,5,5-Tetramethylcyclohex-1-en-1-yl triflateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl2×HCID 57706776Methyl 2'-fluoro-5'-(methyloxy)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl-4-carboxylate

Produkt 1

HCID 57706531HCID 57706531, VerbindungAusbeute 58,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysator2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A screw-cap vial was charged with 66.31A (0.556 g, 1.94 mmol), THF (10 mL), 66.56A (0.500 g, 1.29 mmol), potassium phosphate (0.824 g, 3.88 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (commercially available from Aldrich) (0.165 g, 0.401 mmol), palladium(II) acetate (0.0291 g, 0.129 mmol), and water (0.117 mL, 6.47 mmol). The mixture was purged with argon and stirred for 48 hours at room temperature under an argon balloon. Additional 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.165 g, 0.401 mmol), palladium(II) acetate (0.0291 g, 0.129 mmol), and 69.31A (0.556 g, 1.94 mmol) were added, and stirring was continued for 16 hours at room temperature under argon. The mixture was filtered through silica gel (EtOAc) and concentrated. The crude product was purified by silica gel flash chromatography (0-5% EtOAc/hexane) to afford 69.31B (0.300 g, 58% yield) as a colorless oil.

Aufarbeitung

  1. customThe mixture was purged with argon
  2. stirringstirring
  3. waitwas continued for 16 hours at room temperature under argon
  4. filtrationThe mixture was filtered through silica gel (EtOAc)
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel flash chromatography (0-5% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-88e265bc0dc8409d98c5a8dfe6001736
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030354B2

Notizen zur Reaktion

Wird geladen…