Phosphorus oxybromide → HCID 57506731, compound

HRID 1945580Notes

Reaction equation

HRID 1945580 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[CH:16][N+:15]([O-])=[CH:14][C:13]=3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)([Br:22])=O>C(#N)C.O1CCOCC1>[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[CH:16][N:15]=[C:14]([Br:22])[C:13]=3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 24613Phosphorus oxybromideHCID 59605785HCID 59605785, compound

Product 1

HCID 57506731HCID 57506731, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A 250 mL round-bottomed flask, under nitrogen, fitted with a thermometer probe and a condenser/inert gas bubbler (via a Claisen head), was charged with a solution of 1-benzenesulfonyl-1H-pyrrolo[3,2-c]pyridine 5-oxide (3.5 g, 12.8 mmol) in acetonitrile (50 mL) and dioxane (50 mL). To this solution was added dropwise phosphorus oxybromide (12 g, 40.9 mmol) and the resulting mixture was stirred at 70° C. for 18 h. The precipitate formed was removed by filtration and washed several times with dioxane. The solution was concentrated in vacuo and partitioned between DCM, water and brine. The organic layer was isolated then dried (Na2SO4) and concentrated in vacuo. The resultant residue was purified by flash chromatography (Si—PCC, 0-20% EtOAc in cyclohexane) to give the desired product (3.1 g, 72%). 1H NMR (CDCl3, 300 MHz): δ 8.23 (d, J=5.7 Hz, 1 H); 7.94-7.85 (m, 3 H); 7.67-7.59 (m, 2 H); 7.55-7.48 (m, 2 H); 6.75 (dd, J=3.7, 0.8 Hz, 1 H).

Workup

  1. customA 250 mL round-bottomed flask, under nitrogen, fitted with a thermometer probe
  2. customThe precipitate formed
  3. customwas removed by filtration
  4. washwashed several times with dioxane
  5. concentrationThe solution was concentrated in vacuo
  6. custompartitioned between DCM, water and brine
  7. customThe organic layer was isolated
  8. dry with materialthen dried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customThe resultant residue was purified by flash chromatography (Si—PCC, 0-20% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-7b750460254f4fde8e3621b75267726d
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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