Triphenylphosphine → 5-[(4-Fluorophenyl)carbonyl]-2-[(2-methylpyridin-4-yl)methoxy]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

HRID 571733

Reaktionsgleichung

Reaktionsgleichung von HRID 571733
N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:36][C:37]1[CH:42]=[C:41]([CH2:43][OH:44])[CH:40]=[CH:39][N:38]=1.[F:45][C:46]1[CH:51]=[CH:50][C:49]([C:52]([N:54]2[CH2:59][CH2:58][N:57]3[N:60]=[C:61](O)[CH:62]=[C:56]3[CH2:55]2)=[O:53])=[CH:48][CH:47]=1>C1COCC1>[F:45][C:46]1[CH:47]=[CH:48][C:49]([C:52]([N:54]2[CH2:59][CH2:58][N:57]3[N:60]=[C:61]([O:44][CH2:43][C:41]4[CH:40]=[CH:39][N:38]=[C:37]([CH3:36])[CH:42]=4)[CH:62]=[C:56]3[CH2:55]2)=[O:53])=[CH:50][CH:51]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 9942144(2-Methylpyridin-4-yl)methanolHCID 178519627HCID 178519627, Verbindung

Produkt 1

HCID 727032155-[(4-Fluorophenyl)carbonyl]-2-[(2-methylpyridin-4-yl)methoxy]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazineAusbeute 35,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Di-tert-butyl azodicarboxylate (0.138 g, 0.6 mmol) was added to a stirred solution of triphenylphosphine (0.157 g, 0.6 mmol), (2-methylpyridin-4-yl)methanol (0.074 g, 0.6 mmol) and 5-[(4-fluorophenyl)carbonyl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ol (0.157 g, 0.6 mmol) in THF (3 mL) in a sealed tube and under nitrogen. The mixture was stirred at 130° C. for 20 minutes under microwave irradiation and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica; 7 M solution of ammonia in methanol in DCM 0/100 to 5/95, twice). The desired fractions were collected, the solvents evaporated in vacuo and the residue triturated with DIPE to yield 5-[(4-fluorophenyl)carbonyl]-2-[(2-methylpyridin-4-yl)methoxy]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine (0.078 g, 35% yield) as a white solid. C20H19FN4O2. 1H NMR (400 MHz, CDCl3) δ ppm 2.56 (s, 3 H), 4.08 (br. s., 4 H), 4.74 (br. s., 2 H), 5.17 (s, 2 H), 5.52 (br. s., 1 H), 7.10-7.18 (m, 3 H), 7.21 (br. s, 1 H), 7.45-7.52 (m, 2 H), 8.47 (d, J=5.1 Hz, 1 H).

Aufarbeitung

  1. customthe solvents were evaporated in vacuo
  2. customThe crude product was purified by flash column chromatography (silica
  3. customThe desired fractions were collected
  4. customthe solvents evaporated in vacuo
  5. customthe residue triturated with DIPE

Quellen und Nachweise

ORD-Eintrag
ord-48b4d776c259422cb876f6f6b47b7b98
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029366B2

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