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

HRID 254789Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 254789
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, 1.1 eq. 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-d929aae991e744fd9dbd7f5edc65d337
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875622B2

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