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

HRID 215780Notes

Reaction equation

HRID 215780 reaction equation
[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]

Participants

5

Reactant 2

HCID 24408BromineHCID 42601503Enerisant

Product 1

HCID 42610410[1-(3-Bromo-4-{3-[(2r)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1h-pyrazol-4-yl](morpholin-4-yl)methanoneYield 29.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-10537e5c020f44789dda514523e29e79
Source dataset
uspto-grants-2012_06
Patent number
US08193176B2

Reaction notes

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