Boron tribromide → HCID 178516348, compound

HRID 1374704Notes

Reaction equation

HRID 1374704 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:18]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[C:11]3[CH:12]=[C:13]([O:16]C)[CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:18]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[C:11]3[CH:12]=[C:13]([OH:16])[CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 9966795HCID 9966795, compound

Product 1

HCID 178516348HCID 178516348, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(4-fluorophenyl)-3-(4-pyridyl)-5-methoxypyrazolo[1,5-a]pyridine (Example 5. 0.05 g, 0.16 mmol) in dry CH2Cl2 was cooled to about −78° C. under nitrogen. Boron tribromide (0.8 mL of a 1M solution in CH2Cl2, 0.8 mmol) was added dropwise and the mixture was stirred and warmed to room temperature over about 24 h. Ice was added to the reaction mixture and the resulting slurry was stirred for about 15 min. The CH2Cl2 was evaporated under vacuum and the resulting aqueous slurry was treated with conc hydrochloric acid (1 mL) and stirred. The aqueous solution was basified by the addition of a saturated solution of NaHCO3, and the resulting solid was collected by filtration and was dried under vacuum to give the title compound.

Workup

  1. additionIce was added to the reaction mixture
  2. stirringthe resulting slurry was stirred for about 15 min
  3. customThe CH2Cl2 was evaporated under vacuum
  4. additionthe resulting aqueous slurry was treated with conc hydrochloric acid (1 mL)
  5. stirringstirred
  6. additionThe aqueous solution was basified by the addition of a saturated solution of NaHCO3
  7. filtrationthe resulting solid was collected by filtration
  8. customwas dried under vacuum

Sources & evidence

ORD record
ord-dd0e77e76734498989797dbd8453ac92
Source dataset
uspto-grants-2007_01
Patent number
US07166597B2

Reaction notes

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