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

HRID 1928658Notes

Reaction equation

HRID 1928658 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-38dd87e5da3945369a39334c4a7a3776
Source dataset
uspto-grants-2012_05
Patent number
US08183387B2

Reaction notes

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