Diisopropylethylamine → 1-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-1-yl)-2-methoxy-2-(4-morpholinophenyl)ethanone

HRID 512677Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 512677
[CH3:1][O:2][CH:3]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[C:4]([OH:6])=O.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([C:29]2[CH:33]=[CH:32][NH:31][N:30]=2)[CH:24]=[CH:25][C:26]=1[O:27][CH3:28].C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([C:29]2[CH:33]=[CH:32][N:31]([C:4](=[O:6])[CH:3]([O:2][CH3:1])[C:7]3[CH:12]=[CH:11][C:10]([N:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)=[CH:9][CH:8]=3)[N:30]=2)[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]

Komponenten

7

Edukt 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733179PyBroPHCID 584321092-Methoxy-2-(4-morpholinophenyl)acetic acidHCID 178488676HCID 178488676, Verbindung

Produkt 1

HCID 584320151-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-1-yl)-2-methoxy-2-(4-morpholinophenyl)ethanoneAusbeute 489,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-methoxy-2-(4-morpholinophenyl)acetic acid (0.1 g, 0.42 mmol) and 3-(3,4-dimethoxyphenyl)-1H-pyrazole (0.86 g, 0.42 mmol) in anhydrous DMF (4 mL) at room temperature was added diisopropylethylamine (0.22 ml, 1.26 mmol) then bromotripyrrolidinophosphonium hexafluorophosphate (0.23 g, 0.50 mmol). After 24 hrs, saturated aqueous NaHCO3 was added. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organics were washed with H2O and brine, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (0-60% EtOAc-hexanes) gave 1-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-1-yl)-2-methoxy-2-(4-morpholinophenyl)ethanone as a white solid (0.90 g, 50% yield). MS: m/z 438.2 [M+H]+.

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organics were washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography (0-60% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-93cc5cea40194411b8ed9061a42c7af0
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102643B2

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