Boron tribromide → HCID 67973849, compound

HRID 2046244Notes

Reaction equation

HRID 2046244 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]3[N:14]=[C:15]([CH2:17]OC4C=CC=CC=4)[CH:16]=[C:10]3[C:9]2=[O:25])=[N:6][CH:7]=1.B(Br)(Br)[Br:27]>C(Cl)Cl>[Br:27][CH2:17][C:15]1[CH:16]=[C:10]2[C:9](=[O:25])[N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=3)[CH2:13][CH2:12][N:11]2[N:14]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67974411HCID 67974411, compound

Product 1

HCID 67973849HCID 67973849, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

5-(5-fluoropyridin-2-yl)-2-(phenoxymethyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one (100 mg, 0.296 mmol) was dissolved in DCM (2 mL), cooled to 0° C. and treated with 1M BBr3 in DCM (1.18 mmol, 1.18 mL). The reaction was allowed to warm to room temperature and stirred for 4 h. The reaction was diluted with DCM (5 mL) and then washed sequentially with 1M HCl (2 mL), saturated aq. NaHCO3 (2 mL) and 1N NaOH (2 ml). The organic layer was dried over Na2SO4, filtered and concentrated under vacuum to give A (82 mg, 85%) as an oil: LC-MS (215 nm)>98%, 324.8 (M+H).

Workup

  1. temperatureto warm to room temperature
  2. washwashed sequentially with 1M HCl (2 mL), saturated aq. NaHCO3 (2 mL) and 1N NaOH (2 ml)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto give A (82 mg, 85%) as an oil

Sources & evidence

ORD record
ord-061af7ffccfc4ec8937641cfd2252e3f
Source dataset
uspto-grants-2013_11
Patent number
US08592422B2

Reaction notes

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