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

HRID 348009ノート

反応式

HRID 348009 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 18399249Chloroform dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f6caeffcdbba45e1a538a3a80b67cfa0
出典データセット
uspto-grants-2007_02
特許番号
US07176210B2

反応ノート

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