Dichloromethane → HCID 178515644, compound

HRID 1013838Notes

Reaction equation

HRID 1013838 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([O:24]C)[CH:21]=[CH:20][C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:18][CH2:17][C:16]3[C:12](=[CH:13][NH:14][N:15]=3)[CH2:11]2)[C:6]1=[O:19].B(Br)(Br)Br.C(Cl)Cl>ClC(Cl)C>[Cl:1][C:2]1[CH:23]=[C:22]([OH:24])[CH:21]=[CH:20][C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:18][CH2:17][C:16]3[C:12](=[CH:13][NH:14][N:15]=3)[CH2:11]2)[C:6]1=[O:19]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 178489744HCID 178489744, compound

Product 1

HCID 178515644HCID 178515644, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Cool a solution of 3-(2-Chloro-4-methoxy-benzyl)-1-(4,5,6,7-tetrahydro-2H-indazol-5-yl)-pyrrolidin-2-one (3.0 g, 8.3 mmol) in dichloroethane (100 mL) to −78° C. Treat the solution with 1.0M Boron tribromide in CH2Cl2 (46 mL, 46 mmol) and allow the reaction to warm to room temp and stir for 4 hr. Then, cool the reaction to 0° C. and quench with water. Extract the organic with CHCl3, wash with brine, dry over MgSO4, filter, and remove the solvent. Purify the crude by silica gel column chromatography using 10% EtOH in CHCl3 to elute the pure product. Remove the solvent to afford 2.24 g (78%) of product. MS (m/e): 364 (M+1).

Workup

  1. customthe reaction
  2. temperatureThen, cool
  3. customthe reaction to 0° C.
  4. customquench with water
  5. extractionExtract the organic with CHCl3
  6. washwash with brine
  7. dry with materialdry over MgSO4
  8. filtrationfilter
  9. customremove the solvent
  10. customPurify the crude by silica gel column chromatography
  11. washto elute the pure product
  12. customRemove the solvent

Sources & evidence

ORD record
ord-857dbab9935d4c9b855eb5b412d63137
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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