Ammonium Chloride → 4-cyano-7-fluoro-6-(3-fluorophenyl)-N,N,5-trimethyl-1,3-benzoxazole-2-carboxamide

HRID 17466

Reaktionsgleichung

Reaktionsgleichung von HRID 17466
Br[C:2]1[C:15]([CH3:16])=[C:14]([C:17]#[N:18])[C:5]2[N:6]=[C:7]([C:9]([N:11]([CH3:13])[CH3:12])=[O:10])[O:8][C:4]=2[C:3]=1[F:19].[F:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[C:17]([C:14]1[C:5]2[N:6]=[C:7]([C:9]([N:11]([CH3:13])[CH3:12])=[O:10])[O:8][C:4]=2[C:3]([F:19])=[C:2]([C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([F:20])[CH:26]=2)[C:15]=1[CH3:16])#[N:18]

Komponenten

8

Edukt 4

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 27339863-Fluorophenylboronic acidHCID 685849626-Bromo-4-cyano-7-fluoro-N,N,5-trimethyl-1,3-benzoxazole-2-carboxamide

Produkt 1

HCID 685853994-cyano-7-fluoro-6-(3-fluorophenyl)-N,N,5-trimethyl-1,3-benzoxazole-2-carboxamideAusbeute 36,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

6-Bromo-4-cyano-7-fluoro-N,N,5-trimethyl-1,3-benzoxazole-2-carboxamide (I-127) (200 mg, 0.61 mmol), 3-fluorophenylboronic acid (343 mg, 2.45 mmol) and tripotassium phosphate (261 mg, 1.23 mmol) were suspended in 1,4-dioxane (6 ml), and at room temperature, tetrakis(triphenylphosphine)palladium(0) (142 mg, 0.12 mmol) was added. The suspension was stirred under nitrogen atmosphere at 95° C. for 62 hours, followed by cooling to room temperature. The solution was fractionated with ethyl acetate and aqueous saturated ammonium chloride solution. The aqueous layer was extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=5:2) to obtain the entitled compound (76 mg, 36%) as a white solid.

Aufarbeitung

  1. temperatureby cooling to room temperature
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe insoluble matter was separated by filtration
  6. customthe solvent was evaporated away
  7. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=5:2)

Quellen und Nachweise

ORD-Eintrag
ord-b7966398c9fb41b5938a8a5ce8d80195
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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