Phosphorus trichloride → HCID 135936185, compound

HRID 1881336Notes

Reaction equation

HRID 1881336 reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[C:8]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18][N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[CH:14][N+:13]=3[O-])=[C:9]([OH:11])[NH:10][C:5]2=[CH:4][CH:3]=1.P(Cl)(Cl)Cl>C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[C:6]2[C:8]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18][N:19]4[CH2:20][CH2:21][O:22][CH2:23][CH2:24]4)=[CH:14][N:13]=3)=[C:9]([OH:11])[NH:10][C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24387Phosphorus trichlorideHCID 178526263HCID 178526263, compound

Product 1

HCID 135936185HCID 135936185, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

728 mg of 2-(5-Bromo-2-hydroxy-1H-pyrrolo[3,2-b]pyridin-3-yl)-5-(morpholinomethyl)pyridine 1-oxide from example 4.1 were dissolved in ethyl acetate (20 mL) and 627 μL phosphorus trichloride (7.19 mmol) was added. After stirring the resulting suspension at ambient temperature for 2 days the precipitate was removed by filtration, washed with ethyl acetate, and dissolved in water. The aqueous layer was basified by addition of solid NaHCO3 and extracted with ethyl acetate (6×). The combined organic phases were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude was further purified by flash chromatography yielding the titled compound as a yellow foam (335 mg, 48%).

Workup

  1. customwas removed by filtration
  2. washwashed with ethyl acetate
  3. dissolutiondissolved in water
  4. additionThe aqueous layer was basified by addition of solid NaHCO3
  5. extractionextracted with ethyl acetate (6×)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude was further purified by flash chromatography

Sources & evidence

ORD record
ord-24c5f6a6f7cd4ba2aaaa23651f4d0b78
Source dataset
uspto-grants-2012_11
Patent number
US08318793B2

Reaction notes

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