Trimethylphosphine → HCID 57344512, compound

HRID 2401398Notes

Reaction equation

HRID 2401398 reaction equation
[N:1]([CH:4]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[C:8]2[CH:18]=[CH:19][CH:20]=[CH:21][C:7]=2[C:6]2[C:22]([CH3:25])=[N:23][O:24][C:5]1=2)=[N+]=[N-].CP(C)C>[Cl-].[Na+].O>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[C:8]3[CH:18]=[CH:19][CH:20]=[CH:21][C:7]=3[C:6]3[C:22]([CH3:25])=[N:23][O:24][C:5]=3[CH:4]([NH2:1])[N:10]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 68983TrimethylphosphineHCID 86666724HCID 86666724, compound

Product 1

HCID 57344512HCID 57344512, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A round bottomed flask containing crude 4-azido-6-(4-chlorophenyl)-1-methyl-4H-benzo[c]isoxazolo[4,5-e]azepine (1.05 g, 3.0 mmol), was purged with nitrogen and diluted with THF (30 mL) and water (6 mL). Trimethylphosphine (6.03 mL, 6.0 mmol, 1M in toluene) was added dropwise. The solution was stirred at ambient temperature for 2 h. The reaction was poured into half-saturated brine (100 mL), extracted with EtOAc (3×), dried over Na2SO4, filtered, concentrated and purified on a Biotage system (isocratic elution 65% EtOAc: 35% Hexanes) to provide the title compound as an oil (0.44 g). LC/MS m/z 324 [M+H]+.

Workup

  1. customwas purged with nitrogen
  2. additiondiluted with THF (30 mL) and water (6 mL)
  3. extractionextracted with EtOAc (3×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified on a Biotage system (isocratic elution 65% EtOAc: 35% Hexanes)

Sources & evidence

ORD record
ord-faf011a5458a4828a8cc9edaac9ab36f
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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