Dimethylformamide → Tert-butyl 2-(diphenylmethyleneamino)-3-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate

HRID 419268Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419268
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([N:17]=[C:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[C:4]([F:31])[CH:3]=1.[CH:32]1(P(C2CCCCC2)C2CCCCC2)[CH2:37]CCC[CH2:33]1.[O:51]1CCO[BH:52]1.[CH3:56][C:57]([O-:59])=O.[K+].[CH3:61]N(C=O)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[C:19]1([C:18](=[N:17][CH:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([B:52]3[O:51][C:32]([CH3:37])([CH3:33])[C:57]([CH3:56])([CH3:61])[O:59]3)=[CH:3][C:4]=2[F:31])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

7

Edukt 5

HCID 6228DimethylformamideHCID 75806TricyclohexylphosphineHCID 517044Potassium AcetateHCID 5326306InChI=1/C2H5BO2/c1-2-5-3-4-1/h3H,1-2HHCID 87090002Tert-butyl 3-(4-bromo-2-fluorophenyl)-2-(diphenylmethylene-amino)propanoate

Produkt 1

HCID 87090021Tert-butyl 2-(diphenylmethyleneamino)-3-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysator

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

An Emrys process vial (20 ml) for microwave was charged with tert-butyl 3-(4-bromo-2-fluorophenyl)-2-(diphenylmethylene-amino)propanoate (600 mg, 1.24 mmol), Pd(dba)2 (71 mg, 0.124 mmol), PCy3 (35 mg, 0.124 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane (346 mg, 1.1eq. 1.36 mmol) and KOAc (182 mg, 1.5 eq., 1.86 mmol) 20 ml of DMF. The reaction vessel was sealed and heated to 160° C. for 20 minutes by microwave. After cooling, the reaction mixture was evaporated to dryness under reduced pressure. The residue was dissolved in H2O (30 ml), extracted with EtOAc (2×40 ml), and purified with Prep-LC to give 220 mg of tert-butyl 2-(diphenylmethyleneamino)-3-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate.

Aufarbeitung

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated to dryness under reduced pressure
  4. dissolutionThe residue was dissolved in H2O (30 ml)
  5. extractionextracted with EtOAc (2×40 ml)
  6. custompurified with Prep-LC

Quellen und Nachweise

ORD-Eintrag
ord-4c8c37401c2748028a993e26930c5f30
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093291B2

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