Cesium carbonate → 3-Chloro-5-{[5-chloro-1-(4-methoxybenzyl)-1H-1,2,3-benzotriazol-4-yl]oxy}benzonitrile

HRID 505515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505515
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]([CH2:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=3)[N:7]=[N:8][C:4]=2[C:3]=1[OH:20].F[C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([Cl:30])[CH:29]=1)[C:25]#[N:26].C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1>[Cl:30][C:28]1[CH:27]=[C:24]([CH:23]=[C:22]([O:20][C:3]2[C:4]3[N:8]=[N:7][N:6]([CH2:9][C:10]4[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=4)[C:5]=3[CH:18]=[CH:19][C:2]=2[Cl:1])[CH:29]=1)[C:25]#[N:26]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 27348413-Chloro-5-fluorobenzonitrileHCID 1361332735-Chloro-1-(4-methoxybenzyl)-1H-1,2,3-benzotriazol-4-ol

Produkt 1

HCID 684272083-Chloro-5-{[5-chloro-1-(4-methoxybenzyl)-1H-1,2,3-benzotriazol-4-yl]oxy}benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A stirred suspension of 5-chloro-1-(4-methoxybenzyl)-1H-1,2,3-benzotriazol-4-ol (0.050 g, 0.173 mmol), 3-fluoro-5-chloro-benzonitrile (0.081 g, 0.518 mmol) and cesium carbonate (0.068 g, 0.207 mmol) in NMP (1.5 mL) was heated at 140° C. for 72 hours. The reaction mixture was then quenched with aqueous ammonium chloride (25 mL) and extracted with dichloromethane (2×100 mL). The combined extracts were concentrated under reduced pressure. The resulting residue was subjected to reverse phase chromatography (5-95% MeCN/H2O, 0.1% TFA). The product fractions were combined and extracted with dichloromethane (2×100 mL). The combined extracts were dried over MgSO4, filtered and concentrated under reduced pressure to yield the title product. 1H NMR (DMSO d6) δ 7.90-7.88 (m, 1H), 7.80 (s, 1H), 7.79-7.75 (m, 1H), 7.60-7.55 (m, 2H), 7.40-7.35 (d, J=6.9 Hz, 2H), 6.95-6.88 (m, 2H), 5.80 (s, 2H), 3.71 (s, 3H).

Aufarbeitung

  1. customThe reaction mixture was then quenched with aqueous ammonium chloride (25 mL)
  2. extractionextracted with dichloromethane (2×100 mL)
  3. concentrationThe combined extracts were concentrated under reduced pressure
  4. extractionextracted with dichloromethane (2×100 mL)
  5. dry with materialThe combined extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-82a6d767f38e412fb2af7b030baebcce
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781454B2

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