Triphenylphosphine → HCID 58216644, compound

HRID 1799591Notes

Reaction equation

HRID 1799591 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[N:8][O:9][N+:10]=2[O-])[N:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[N:8][O:9][N:10]=2)[N:7]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 85766671HCID 85766671, compound

Product 1

HCID 58216644HCID 58216644, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

In a dry flask, 5-chloro[1,2,5]oxadiazolo[3,4-b]pyridine 1-oxide (200 mg, 1.166 mmol) and triphenylphosphine (459 mg, 1.749 mmol) were taken-up in dichloromethane (11.7 ml) under argon. The mixture was stirred at 35° C. for 24 hours. The reaction was quenched with 1.0 M aqueous sodium hydroxide and extracted three times with ethyl acetate. All organic fractions were combined, dried over anhydrous magnesium sulfate, and concentrated. The crude product was purified by reverse-phase HPLC (20-100% acetonitrile/water with 0.05% trifluoroacetic acid), and then the appropriate fractions were neutralized with aqueous sodium bicarbonate and washed twice with ethyl acetate. All organic fractions were combined, dried over anhydrous magnesium sulfate, and concentrated to afford 5-chloro[1,2,5]oxadiazolo[3,4-b]pyridine. LRMS (APCI) calc'd for (C5H3ClN2O) [M+H]+, 156. found 156.

Workup

  1. customThe reaction was quenched with 1.0 M aqueous sodium hydroxide
  2. extractionextracted three times with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by reverse-phase HPLC (20-100% acetonitrile/water with 0.05% trifluoroacetic acid)
  6. washwashed twice with ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d9c23b957811407b8c7df9131189b73e
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

Loading…