Boron tribromide → HCID 18671523, compound

HRID 276782Notes

Reaction equation

HRID 276782 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([C:13]2[NH:17][C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([N:24]4[CH2:29][CH2:28][N:27]([CH:30]([CH3:32])[CH3:31])[CH2:26][CH2:25]4)[CH:19]=3)=[N:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1>ClCCl>[OH:6][C:7]1[CH:8]=[C:9]([C:13]2[NH:17][C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([N:24]4[CH2:25][CH2:26][N:27]([CH:30]([CH3:32])[CH3:31])[CH2:28][CH2:29]4)[CH:19]=3)=[N:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18671566HCID 18671566, compound

Product 1

HCID 18671523HCID 18671523, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide (25 mL of a 1 M solution in dichloromethane) was added to a solution of 1-{4-[5(3-methoxy-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-4-isopropyl-piperazine (1.94 g) in dichloromethane. The resultant yellow suspension was kept at ambient temperature overnight and then quenched by the addition of ice and diluted with water. The resultant mixture was stirred for 30 min and then filtered. The filtrate was extracted with 3N HCl, the solids that had been removed were recombined with the aqueous extracts, and the pH was adjusted to 8 with saturated NaHCO3. The resultant mixture was extracted with 9:1 chloroform/methanol. The combined extracts were concentrated in vacuo, and the residue was concentrated from methanol to provide 1-{4-[5(3-Hydroxy-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-4-isopropyl-piperazine (quantitative).

Workup

  1. customquenched by the addition of ice
  2. additiondiluted with water
  3. filtrationfiltered
  4. extractionThe filtrate was extracted with 3N HCl
  5. customthe solids that had been removed
  6. extractionThe resultant mixture was extracted with 9:1 chloroform/methanol
  7. concentrationThe combined extracts were concentrated in vacuo
  8. concentrationthe residue was concentrated from methanol

Sources & evidence

ORD record
ord-c7ea1d42f25e4ddd9e030fa1f163d83e
Source dataset
uspto-grants-2002_03
Patent number
US06355635B1

Reaction notes

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