Trifluoroacetic acid → 3-(3-(1-benzyl-1H-pyrazol-4-yl)pyridin-2-yloxy)-N-(3-isopropylphenyl)-4-methylbenzamide

HRID 883027Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 883027
[OH:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([CH3:16])[CH3:15])[CH:9]=1)=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:27]([N:34]1[CH:38]=[C:37]([C:39]2[C:40](Cl)=[N:41][CH:42]=[CH:43][CH:44]=2)[CH:36]=[N:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O)(C(F)(F)F)=O>CCOC(C)=O.O>[CH2:27]([N:34]1[CH:38]=[C:37]([C:39]2[C:40]([O:1][C:2]3[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=3[CH3:20])[C:5]([NH:7][C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([CH3:16])[CH3:15])[CH:9]=3)=[O:6])=[N:41][CH:42]=[CH:43][CH:44]=2)[CH:36]=[N:35]1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 10796Cesium carbonateHCID 288804893-hydroxy-N-(3-isopropylphenyl)-4-methylbenzamideHCID 866237863-(1-benzyl-1H-pyrazol-4-yl)-2-chloropyridine

Produkt 1

HCID 251022303-(3-(1-benzyl-1H-pyrazol-4-yl)pyridin-2-yloxy)-N-(3-isopropylphenyl)-4-methylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

3-Hydroxy-N-(3-isopropylphenyl)-4-methylbenzamide (100 mg, 0.371 mmol), cesium carbonate (220 mg, 0.676 mmol) and 3-(1-benzyl-1H-pyrazol-4-yl)-2-chloropyridine (91.0 mg, 0.338 mmol) were combined in an argon-purged sealed tube. DMSO (1.5 mL) was added and the mixture was heated to 130° C. for 23 hours. The cooled reaction was diluted with EtOAc and water and then neutralized with TFA (pH˜7). The separated organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified first by silica gel chromatography (1:1 MTBE/benzene) followed by trituration of the resulting solid with 20:1 hexanes/EtOAc to yield 3-(3-(1-benzyl-1H-pyrazol-4-yl)pyridin-2-yloxy)-N-(3-isopropylphenyl)-4-methylbenzamide as an off-white solid. MS m/z=503 [M+1]+. Calc'd for C32H30N4O2: 502.62.

Aufarbeitung

  1. custompurged
  2. customsealed tube
  3. additionDMSO (1.5 mL) was added
  4. customThe cooled reaction
  5. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified first by silica gel chromatography (1:1 MTBE/benzene)

Quellen und Nachweise

ORD-Eintrag
ord-62b4752bf96b4874951a3ddd7db92e57
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236823B2

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