Phosphorus tribromide → HCID 86680615, compound

HRID 1497441Notes

Reaction equation

HRID 1497441 reaction equation
O[CH:2]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[O:16])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[CH2:3][CH3:4].P(Br)(Br)[Br:21]>C(Cl)(Cl)Cl.O>[Br:21][CH:2]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[O:16])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 86680614HCID 86680614, compound

Product 1

HCID 86680615HCID 86680615, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To a solution of 4-(6-(1-hydroxypropyl)pyridin-3-yl)benzamide (0.1 g, 0.39 mmol) in chloroform (15 mL) was added PBr3 (0.316 g, 1.17 mmol) at 0-5° C. The solution was maintained at the same temperature for 1 h, was slowly warmed to rt and maintained at rt for another 2 h. The contents were diluted with water (75 mL) and chloroform (100 mL), the layers separated, the organic layer was washed with bicarbonate solution (2×30 mL), and the organic layer was dried over sodium sulphate and distilled off to get the crude product. The non-polar impurity was removed by pentane washings (2×7 mL) to provide 4-(6-(1-bromopropyl)pyridin-3-yl)benzamide (0.12 g, crude). LC-MS m/z calcd for [M+H]+ 321.03. found 321.0.

Workup

  1. temperatureThe solution was maintained at the same temperature for 1 h
  2. temperaturemaintained at rt for another 2 h
  3. customthe layers separated
  4. washthe organic layer was washed with bicarbonate solution (2×30 mL)
  5. dry with materialthe organic layer was dried over sodium sulphate
  6. distillationdistilled off
  7. customto get the crude product
  8. customThe non-polar impurity was removed by pentane washings (2×7 mL)

Sources & evidence

ORD record
ord-b05c816f593246ba9a86807a0787c7bb
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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