Triphenylphosphine → 7-[(2-Chloro-6-fluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic Acid ethyl Ester

HRID 1486302

Reaktionsgleichung

Reaktionsgleichung von HRID 1486302
[OH:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:16])[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:6]2[CH:5]=[C:4]([CH3:17])[CH:3]=1.[Cl:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:20]=1[CH2:21]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH2:14]([O:13][C:11]([C:10]1[C:9]([CH3:16])=[N:8][N:7]2[C:2]([O:1][CH2:21][C:20]3[C:23]([F:27])=[CH:24][CH:25]=[CH:26][C:19]=3[Cl:18])=[CH:3][C:4]([CH3:17])=[CH:5][C:6]=12)=[O:12])[CH3:15]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 918682-Chloro-6-fluorobenzyl alcoholHCID 178469270HCID 178469270, Verbindung

Produkt 1

HCID 1178646837-[(2-Chloro-6-fluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic Acid ethyl EsterAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 180 mg (0.76 mmol) of 7-hydroxy-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester (Example 8A) in 7 ml of tetrahydrofuran was admixed with 247 mg (1.52 mmol) of 2-chloro-6-fluorobenzyl alcohol, 419 mg (1.60 mmol) of triphenylphosphine and 0.32 ml (1.60 mmol) of diisopropyl azodicarboxylate. The reaction mixture was stirred at room temperature for 1 h and concentrated under reduced pressure. The residue was purified by flash chromatography using a prepacked silica gel cartridge (mobile phase: cyclohexane-ethyl acetate, gradient 10% to 30%), which gave 280 mg (84% yield, 84% pure) of the target compound.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by flash chromatography
  3. customgave 280 mg (84% yield, 84% pure) of the target compound

Quellen und Nachweise

ORD-Eintrag
ord-7ab9d557bc7a42c0ade9b937f93ea9fa
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422285B2

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