Pentapotassium Triphosphate → HCID 57516918, Verbindung

HRID 62537

Reaktionsgleichung

Reaktionsgleichung von HRID 62537
[Cl:1][C:2]1[CH:7]=[C:6](I)[C:5]([Cl:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:12]=1[C:13]#[N:14].[O-]P(OP(OP([O-])([O-])=O)([O-])=O)(=O)[O-].[K+].[K+].[K+].[K+].[K+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C(OC3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=CC=3)=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:10][C:11]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:12]=2[C:13]#[N:14])[C:5]([Cl:9])=[CH:4][N:3]=1

Komponenten

7

Edukt 3

HCID 61695Pentapotassium TriphosphateHCID 27377042-Amino-5-fluorobenzonitrileHCID 534009652,5-Dichloro-4-iodopyridine

Produkt 1

HCID 57516918HCID 57516918, VerbindungAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a degassed solution of 2,5-dichloro-4-iodopyridine (8 g, 29.2 mmol), 2-amino-5-fluorobenzonitrile (3.98 g, 29.2 mmol) and potassium triphosphate (18.60 g, 88 mmol) in 1,4-dioxane (100 ml) stirred under nitrogen at the room temperature was added DPEPhos (1.258 g, 2.337 mmol) and palladium acetate (0.262 g, 1.168 mmol). The reaction mixture was stirred at the reflux for 18 hr. The reaction mixture was filtered. The solvent was evaporated. Ether (50 ml) was added and the solid was filtered. 2-[(2,5-Dichloro-4-pyridinyl)amino]-5-fluorobenzonitrile (7.09 g, 25.1 mmol, 86% yield) was isolated as an orange solid. 1H NMR (400 MHz, METHANOL-d4) ppm 6.44 (s, 1 H) 7.46-7.58 (m, 2 H) 7.66 (dd, J=8.08, 2.78 Hz, 1 H) 8.08 (s, 1 H); HPLC Rt=3.23 min, MS (ESI): 382.0, 384.19 [M+H]+.

Aufarbeitung

  1. temperaturereflux for 18 hr
  2. filtrationThe reaction mixture was filtered
  3. customThe solvent was evaporated
  4. additionEther (50 ml) was added
  5. filtrationthe solid was filtered

Quellen und Nachweise

ORD-Eintrag
ord-96223665d9f24db18761ea870c899c22
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09446034B2

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