Dimethylformamide → 5-[3-(2,4-Difluorophenyl)-[1,2,4]triazin-5-yl]-2-fluorobenzonitrile

HRID 1064279Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1064279
Br[C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=3[F:22])[N:12]=[N:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:23][N:24](C)C=O>[C-]#N.[Zn+2].[C-]#N.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>[F:22][C:16]1[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:15]=1[C:11]1[N:12]=[N:13][CH:14]=[C:9]([C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([CH:3]=2)[C:23]#[N:24])[N:10]=1

Komponenten

5

Edukt 2

HCID 6228DimethylformamideHCID 103842555-(3-Bromo-4-fluorophenyl)-3-(2,4-difluorophenyl)-[1,2,4]triazine

Produkt 1

HCID 99727745-[3-(2,4-Difluorophenyl)-[1,2,4]triazin-5-yl]-2-fluorobenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 5-(3-bromo-4-fluorophenyl)-3-(2,4-difluorophenyl)-[1,2,4]triazine (0.1 g, 0.27 mmol), zinc cyanide (0.032 g, 0.27 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.016 g, 0.01 mmol) in N,N-dimethylformamide (4 ml) was heated to 150° C. Fog 600 s in a Smith Synthesiser microwave reactor (Personal Chemistry, Uppsala, Sweden). The reaction was partitioned between ethyl acetate (80 ml) and water (40 ml). The organic layer was washed with water (40 ml) and the combined organics dried over Mg2SO4, filtered and the solvent removed at reduced pressure. The crude product was chromatographed on silica gel, eluent 50% ethyl acetate in isohexane, to give 5-[3-(2,4-difluorophenyl)-[1,2,4]triazin-5-yl]-2-fluorobenzonitrile as a yellow solid (0.054 g): δH (400 MHz, CDCl3) 7.02-7.14 (2H, m), 7.48 (1H, t, J 8.6 Hz), 8.33-8.39 (1H, m), 8.49-8.53 (1H, m), 8.62 (1H, dd, J 2.2, 6.1 Hz), 9.65 (1H, s); m/z(ES+) 313.

Aufarbeitung

  1. customFog 600 s
  2. customThe reaction was partitioned between ethyl acetate (80 ml) and water (40 ml)
  3. washThe organic layer was washed with water (40 ml)
  4. dry with materialthe combined organics dried over Mg2SO4
  5. filtrationfiltered
  6. customthe solvent removed at reduced pressure
  7. customThe crude product was chromatographed on silica gel, eluent 50% ethyl acetate in isohexane

Quellen und Nachweise

ORD-Eintrag
ord-6301ba235f3342028f393f4d3d68d8bf
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06969716B2

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