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

HRID 348009노트

반응식

HRID 348009 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 18399249Chloroform dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f6caeffcdbba45e1a538a3a80b67cfa0
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176210B2

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