Acetyl chloride → N-[5-(5-Cyanopyridin-3-ylethynyl)-2-fluorophenyl]-acetamide

HRID 606955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606955
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][C:11]2[CH:12]=[N:13][CH:14]=[C:15]([CH:18]=2)[C:16]#[N:17])[CH:5]=[CH:6][C:7]=1[F:8].[C:19](Cl)(=[O:21])[CH3:20]>N1C=CC=CC=1.O1CCCC1.O>[C:16]([C:15]1[CH:18]=[C:11]([C:10]#[C:9][C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([NH:1][C:19](=[O:21])[CH3:20])[CH:3]=2)[CH:12]=[N:13][CH:14]=1)#[N:17]

Komponenten

6

Edukt 2

HCID 6367Acetyl chlorideHCID 670478225-(3-Amino-4-fluorophenylethynyl)-nicotinonitrile

Produkt 1

HCID 67048361N-[5-(5-Cyanopyridin-3-ylethynyl)-2-fluorophenyl]-acetamideAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Dissolve 5-(3-amino-4-fluorophenylethynyl)-nicotinonitrile, (prepared as described in EXAMPLE 160), (0.2 g, 0.8 mmol) in anhydrous pyridine. A solution of acetyl chloride (0.07 g, 0.88 mmol) in tetrahydrofuran is added to the reaction and stirred overnight at room temperature. Concentrate and dissolve the crude reaction in ethyl acetate and water. Wash the organic layer with water, an aqueous saturated solution of sodium chloride, dry (potassium carbonate), filter, concentrate and purify (silica gel chromatography, eluting with 95:5 to 80:20 dichloromethane:ethyl acetate), to give the title compound as a white solid (180 mg, 81%).

Aufarbeitung

  1. concentrationConcentrate
  2. dissolutiondissolve the crude
  3. customreaction in ethyl acetate
  4. washWash the organic layer with water
  5. dry with materialan aqueous saturated solution of sodium chloride, dry (potassium carbonate)
  6. filtrationfilter
  7. concentrationconcentrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with 95:5 to 80:20 dichloromethane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-9ef8a5587dac4043a119d3848e1ccba0
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915424B2

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