P,P-Diphenylphosphinic azide → HCID 86610991, compound

HRID 2354062Notes

Reaction equation

HRID 2354062 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:10]=1)[C:5](O)=[O:6].C1C=CC(P([N:33]=[N+:34]=[N-:35])(C2C=CC=CC=2)=O)=CC=1>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:10]=1)[C:5]([N:33]=[N+:34]=[N-:35])=[O:6]

Participants

4

Reactant 2

HCID 199401P,P-Diphenylphosphinic azideHCID 68693732HCID 68693732, compound

Product 1

HCID 86610991HCID 86610991, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-methyl-6-(E)-styryl-isonicotinic acid (214 mg, 0.89 mmol) in DMF (5 mL) is added at 0° C. TEA (0.21 mL, 1.5 mmol) and slowly (30 min) DPPA (366 mg, 1.33 mmol). The reaction mixture is stirred for 0.5 h at 0° C. and 0.5 h at r.t. The reaction is quenched with ice (20 g) and extracted with Et2O (6×30 mL). The combined organic extracts are washed successively with saturated NaHCO3 (2×15 mL) and water (2×10 mL), and are evaporated in vacuo without heating. The residue is purified by FC (SiO2, EtOAc-heptane) to provide the title compound.

Workup

  1. customThe reaction is quenched with ice (20 g)
  2. extractionextracted with Et2O (6×30 mL)
  3. washThe combined organic extracts are washed successively with saturated NaHCO3 (2×15 mL) and water (2×10 mL)
  4. customare evaporated in vacuo
  5. temperaturewithout heating
  6. customThe residue is purified by FC (SiO2, EtOAc-heptane)

Sources & evidence

ORD record
ord-a8201cc12a6848f7a294edd4daaf6af0
Source dataset
uspto-grants-2010_07
Patent number
US07750161B2

Reaction notes

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