Bromine → [1-(3-Bromo-4-{3-[(2r)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1h-pyrazol-4-yl](morpholin-4-yl)methanone

HRID 1364230Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1364230
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[O:23])[CH:19]=[N:18]2)=[CH:13][CH:12]=1.[Br:30]Br>C(O)(=O)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>[Br:30][C:12]1[CH:13]=[C:14]([N:17]2[CH:21]=[C:20]([C:22]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)=[O:23])[CH:19]=[N:18]2)[CH:15]=[CH:16][C:11]=1[O:10][CH2:9][CH2:8][CH2:7][N:3]1[CH2:4][CH2:5][CH2:6][C@H:2]1[CH3:1]

Komponenten

5

Edukt 2

HCID 24408BromineHCID 42601503Enerisant

Produkt 1

HCID 42610410[1-(3-Bromo-4-{3-[(2r)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1h-pyrazol-4-yl](morpholin-4-yl)methanoneAusbeute 29,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 24477Sodium ThiosulfateLösungsmittel

Versuchsvorschrift

To a solution of 4-{[1-(4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1H-pyrazol-4-yl]carbonyl}morpholine obtained in Example 6 (0.500 g) in acetic acid (8.0 ml), bromine (0.200 g) was added dropwise and stirred overnight at room temperature. The reaction mixture was diluted with saturated aqueous sodium thiosulfate and concentrated under reduced pressure. The resulting residue was diluted with saturated aqueous sodium bicarbonate and extracted with chloroform. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=1:1) to give the titled compound (0.175 g) as a colorless solid.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. additionThe resulting residue was diluted with saturated aqueous sodium bicarbonate
  3. extractionextracted with chloroform
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-f2bc40ae71cc4d258133ca1aedbe5fc7
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888354B2

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