N-Iodosuccinimide → 5-Chloro-7-(3,4-difluorophenyl)-3-iodo-2-methylpyrazolo[1,5-a]pyrimidine

HRID 872088Notes

Reaction equation

HRID 872088 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([F:15])[CH:9]=2)[N:5]2[N:16]=[C:17]([CH3:19])[CH:18]=[C:4]2[N:3]=1.[I:20]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([F:15])[CH:9]=2)[N:5]2[N:16]=[C:17]([CH3:19])[C:18]([I:20])=[C:4]2[N:3]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 866880035-Chloro-7-(3,4-difluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 866880045-Chloro-7-(3,4-difluorophenyl)-3-iodo-2-methylpyrazolo[1,5-a]pyrimidineYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Chloro-7-(3,4-difluorophenyl)-2-methylpyrazolo[1,5-a]pyrimidine (301 mg) is dissolved in CH2Cl2 (50 mL). N-Iodosuccinimide (NIS, 500 mg) is added to the reaction solution. The reaction mixture is stirred at room temperature for about 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 the target compound (301 mg) is yielded by column chromatography. 1H NMR (CDCl3, 300 MHz) δ 8.04 (m, 1H), 7.78 (m, 1H), 7.38 (q, J=8.7 Hz, 1H), 6.85 (s, 1H), 2.51 (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

Sources & evidence

ORD record
ord-63e41ce65cf348faaf5de8356fcd9b33
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

Loading…