Ammonium formate → 3-(Benzyloxy)-5-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 1989961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1989961
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:31])[C:9]2[CH:14]=[C:13]([O:15]CC3C=CC=CC=3)[CH:12]=[C:11]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:10]=2)=[N:3]1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[OH:15][C:13]1[CH:14]=[C:9]([CH:10]=[C:11]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:12]=1)[C:8]([NH:7][C:4]1[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=1)=[O:31]

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 53629651N-(1-methyl-1H-pyrazol-3-yl)-3,5-bis[(phenylmethyl)oxy]benzamide

Produkt 1

HCID 591271193-(Benzyloxy)-5-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)benzamideAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A suspension of N-(1-methyl-1H-pyrazol-3-yl)-3,5-bis[(phenylmethyl)oxy]benzamide (1.0 g, 2.42 mmol) was dissolved in ethanol (12 mL) and ammonium formate (229 mg, 3.63 mmol) was added in one portion. The reaction was blanketed with argon and 10% palladium on activated carbon (10 mg) was added. This mixture was heated to 140° C. for 5 minutes in a Smith Creator microwave. The catalyst was filtered off and the volatiles removed in vacuo, the residue was chromatographed on silica, eluting with a gradient of 30-100% ethyl acetate in iso-hexane, to give the title compound as a white solid (378 mg).

Aufarbeitung

  1. additionwas added
  2. filtrationThe catalyst was filtered off
  3. customthe volatiles removed in vacuo
  4. customthe residue was chromatographed on silica
  5. washeluting with a gradient of 30-100% ethyl acetate in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-1bbaceb4cd754a298e7c7b8b4e042fed
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07642263B2

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