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

HRID 348009Notes

Reaction equation

HRID 348009 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[CH:10]=[C:6]2[N:5]=[C:4]([CH3:18])[CH:3]=1.[I:19]N1C(=O)CCC1=O>C(Cl)Cl.C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:10]([I:19])=[C:6]2[N:5]=[C:4]([CH3:18])[CH:3]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 210837187-Chloro-2-(2-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 210837167-Chloro-2-(2-chlorophenyl)-3-iodo-5-methylpyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 18399249Chloroform dichloromethaneSolvent

Procedure

To a solution of 7-chloro-2-(2-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidine (I-1A-3g; 370 mg, 1.33 mmol) in 5:1 methylene chloride/chloroform (9 ml) cooled in an ice bath was added N-iodosuccinimide (449 mg, 2.0 mmol), portionwise, to give a heterogeneous mixture. After 1.5 hours, the ice bath was removed and the reaction was stirred an additional 2.5 hours to give a homogenous, pink solution. The reaction was extracted from aqueous NaHCO3 with methylene chloride. The combined extracts were washed with saturated aqueous Na2S2O4 and brine, dried (MgSO4), and then concentrated, in vacuo, to afford product I-1A-3h as a tan solid (535 mg, quantitative): +ESI MS (M+1) 403.9; 1H NMR (400 MHz, CD2Cl2) δ 7.57–7.40 (m, 4H), 6.99 (s, 1H), 2.66 (s, 3H).

Workup

  1. customportionwise, to give a heterogeneous mixture
  2. customthe ice bath was removed
  3. customto give a homogenous, pink solution
  4. extractionThe reaction was extracted from aqueous NaHCO3 with methylene chloride
  5. washThe combined extracts were washed with saturated aqueous Na2S2O4 and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated, in vacuo
  8. customto afford product I-1A-3h as a tan solid (535 mg, quantitative)

Sources & evidence

ORD record
ord-f6caeffcdbba45e1a538a3a80b67cfa0
Source dataset
uspto-grants-2007_02
Patent number
US07176210B2

Reaction notes

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