Boron tribromide → HCID 18671523, compound

HRID 1057316Notes

Reaction equation

HRID 1057316 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). MS m/z 378 (M++1).

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-564abe5ec85242a3a22bde4cda2a4f08
Source dataset
uspto-grants-2003_02
Patent number
US06514966B2

Reaction notes

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