Trimethylphosphine → HCID 58368532, compound

HRID 1192704Notes

Reaction equation

HRID 1192704 reaction equation
[N:1]([CH:4]([C:6]1[CH:14]=[C:13]([Cl:15])[C:9]2=[CH:10][O:11][N:12]=[C:8]2[C:7]=1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=1)[CH3:5])=[N+]=[N-].CP(C)C>O1CCCC1.O>[Cl:15][C:13]1[C:9]2=[CH:10][O:11][N:12]=[C:8]2[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[C:6]([CH:4]([NH2:1])[CH3:5])[CH:14]=1

Participants

5

Reactant 2

HCID 68983TrimethylphosphineHCID 58368505HCID 58368505, compound

Product 1

HCID 58368532HCID 58368532, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 6-(1-azidoethyl)-4-chloro-7-(3-fluorophenyl)-2,1-benzisoxazole (90. mg, 0.28 mmol) in tetrahydrofuran (2 mL) and water (0.3 mL) was added 1.0 M trimethylphosphine in THF (0.35 mL, 0.35 mmol). The mixture was stirred at room temperature for 1 hour. After degassing with nitrogen, the reaction mixture was extracted with dichloromethane. The extracts were washed with brine, dried over magnesium sulfate and evaporated to dryness. The crude residue was used directly in the next step (68 mg, 82%). LCMS calculated for C15H10ClFNO (M−NH2)+: m/z=274.1; Found: 274.0.

Workup

  1. customAfter degassing with nitrogen
  2. extractionthe reaction mixture was extracted with dichloromethane
  3. washThe extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-3c9b84d6341d418b8e5777cdbd3f3828
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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