Trifluoroacetic acid → 1H-Pyrazolo[3,4-b]pyridine, 4-(2-fluoro-4-nitrophenoxy)-

HRID 2241185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2241185
COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:19]=4[F:27])=[C:11]3[CH:10]=[N:9]2)=CC=1.C(O)(C(F)(F)F)=O>>[F:27][C:19]1[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:18]=1[O:17][C:16]1[CH:15]=[CH:14][N:13]=[C:12]2[NH:8][N:9]=[CH:10][C:11]=12

Komponenten

3

Edukt 2

HCID 6422Trifluoroacetic acidHCID 672207711-(4-methoxybenzyl)-4-(2-fluoro-4-nitrophenoxy)-1H-pyrazolo[3,4-b]pyridine

Produkt 1

HCID 672218811H-Pyrazolo[3,4-b]pyridine, 4-(2-fluoro-4-nitrophenoxy)-Ausbeute 97,4 %

Versuchsvorschrift

A stirred mixture of 1-(4-methoxybenzyl)-4-(2-fluoro-4-nitrophenoxy)-1H-pyrazolo[3,4-b]pyridine (27.6 g, 70.0 mmol; obtained from Example 1, Step C) and TFA (53.9 mL, 700 mmol) was heated to reflux for 18 hours under N2. The reaction was allowed to cool to room temperature, and then concentrated in vacuo using toluene (4×100 mL) to azeotrope residual TFA. The residue was diluted with EtOAc (200 mL) and carefully neutralized (pH=8-9) with saturated aqueous NaHCO3 (100 mL). The biphasic suspension was stirred at room temperature for 30 minutes. The suspension was filtered. The resulting solid was dried by toluene azeotrope (2×200 mL) to obtain the product (18.7 g, 97%). 1H NMR (DMSO-d6, 400 MHz) δ 13.85 (br s, 1H), 8.40 (m, 2H), 8.15 (m, 1H), 7.91 (s, 1H), 7.66 (m, 1H), 6.65 (m, 1H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours under N2
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with EtOAc (200 mL)
  5. filtrationThe suspension was filtered
  6. dry with materialThe resulting solid was dried by toluene

Quellen und Nachweise

ORD-Eintrag
ord-6583e19216b34458bb4d2112973a205e
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723330B2

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