N-Iodosuccinimide → HCID 86688012, compound

HRID 872111Notes

Reaction equation

HRID 872111 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)[N:5]2[N:15]=[C:16]([CH3:18])[CH:17]=[C:4]2[N:3]=1.[I:19]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)[N:5]2[N:15]=[C:16]([CH3:18])[C:17]([I:19])=[C:4]2[N:3]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 86688011HCID 86688011, compound

Product 1

HCID 86688012HCID 86688012, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Chloro-7-(3-methylphenyl)-2-methylpyrazolo[1,5-a]pyrimidine (381 mg) is dissolved in CH2Cl2 (70 mL) and N-iodosuccinimide (NIS, 467 mg) is added to the reaction solution. The reaction mixture is stirred at room temperature for 16 hours. The reaction solvent is removed by distillation under reduced pressure. The remainder is extracted with ethyl acetate and water. The extracted organic layer is washed with 1 M NaHCO3 aqueous solution and brine and dehydrated with anhydrous MgSO4. The dehydrated organic layer is distilled under reduced pressure and purified by column chromatography to yield the target compound (580 mg). 1H NMR (CDCl3, 300 MHz) δ 7.76 (m, 2H), 7.45 (m, 3H), 6.84 (s, 1H), 2.50 (s, 3H), 2.46 (s, 3H).

Workup

  1. customThe reaction solvent is removed by distillation under reduced pressure
  2. extractionThe remainder is extracted with ethyl acetate and water
  3. washThe extracted organic layer is washed with 1 M NaHCO3 aqueous solution and brine
  4. distillationThe dehydrated organic layer is distilled under reduced pressure
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-440a8b3b03464fb39ea7cf71c170a860
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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