Potassium Phosphate, Tribasic → 2-Cyclopropyl-7-fluoro-5-methyl-6-(thiophen-3-yl)-1,3-benzoxazole-4-carbonitrile

HRID 17596

Reaktionsgleichung

Reaktionsgleichung von HRID 17596
Br[C:2]1[C:3]([F:17])=[C:4]2[O:8][C:7]([CH:9]3[CH2:11][CH2:10]3)=[N:6][C:5]2=[C:12]([C:15]#[N:16])[C:13]=1[CH3:14].[S:18]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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>[CH:9]1([C:7]2[O:8][C:4]3[C:5](=[C:12]([C:15]#[N:16])[C:13]([CH3:14])=[C:2]([C:20]4[CH:21]=[CH:22][S:18][CH:19]=4)[C:3]=3[F:17])[N:6]=2)[CH2:11][CH2:10]1

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 581760Thiophene-3-boronic acidHCID 510414276-Bromo-2-cyclopropyl-7-fluoro-5-methylbenzoxazole-4-carbonitrile

Produkt 1

HCID 685850412-Cyclopropyl-7-fluoro-5-methyl-6-(thiophen-3-yl)-1,3-benzoxazole-4-carbonitrileAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

6-Bromo-2-cyclopropyl-7-fluoro-5-methylbenzoxazole-4-carbonitrile (I-77) (200 mg, 0.68 mmol), 3-thiopheneboronic acid (347 mg, 2.71 mmol) and tripotassium phosphate (288 mg, 1.36 mmol) were suspended in 1,4-dioxane (8 ml), and at room temperature, tetrakis(triphenylphosphine)palladium(0) (157 mg, 0.14 mmol) was added. The mixture liquid was stirred under nitrogen atmosphere at 95° C. for 61 hours, then cooled to room temperature. The insoluble matter was separated by filtration with washing with ethyl acetate, and the filtrate was washed with saturated brine. The organic layer was 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, n-hexane:ethyl acetate=19:1, v/v) to obtain the entitled compound (99 mg, 49%) as a white solid.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customThe insoluble matter was separated by filtration
  3. washwith washing with ethyl acetate
  4. washthe filtrate was washed with saturated brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customThe insoluble matter was separated by filtration
  7. customthe solvent was evaporated away
  8. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-8832c5c1b1f84236b9d82b1e376ededd
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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