Dimethylformamide → HCID 59410531, compound

HRID 1944982Notes

Reaction equation

HRID 1944982 reaction equation
O=P(Cl)(Cl)Cl.[F:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[N:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1.CN([CH:24]=[O:25])C>>[F:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[N:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH:24]=[O:25]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 27811271-(2-fluoro-5-nitrophenyl)-1H-pyrrole

Product 1

HCID 59410531HCID 59410531, compoundYield 54%

Procedure

Anhydrous DMF (0.82 mL, 10.67 mmol) and POCl3 (0.96 mL, 10.67 mmol) were combined at 0° C. in a 50 mL round bottomed flask. The suspension was warmed to ambient temperature and treated with 1-(2-fluoro-5-nitrophenyl)-1H-pyrrole (2.0 g, 9.7 mmol) as a light yellow solution in anhydrous DMF (8 mL). The resulting mixture was vigorously stirred at room temperature for 5 hours. TLC analysis of the mixture after 5 hours showed the complete conversion of the starting material to the product. The reaction mixture was transferred to a separatory funnel and partitioned (EtOAc//H2O). The organic phase was washed with H2O (3×50 mL), brine (3×50 mL), dried over Na2SO4 and evaporated in vacuo to give a brown residue. The residue was purified by flash chromatography (hexanes→1:1 EtOAc/hexanes) to furnish the title compound as a white solid (1.2 g, 54%).

Workup

  1. waitTLC analysis of the mixture after 5 hours showed
  2. customThe reaction mixture was transferred to a separatory funnel
  3. custompartitioned (EtOAc//H2O)
  4. washThe organic phase was washed with H2O (3×50 mL), brine (3×50 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo
  7. customto give a brown residue
  8. customThe residue was purified by flash chromatography (hexanes→1:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-5b9525797091485295750944a1942745
Source dataset
uspto-grants-2013_03
Patent number
US08394951B2

Reaction notes

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