2-Iodobutane → 1-sec-butyl-4-iodo-5-(2-thienyl)-1H-pyrazole

HRID 2359082노트

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HRID 2359082 반응식
[I:1][C:2]1[C:3]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)=[N:4][NH:5][CH:6]=1.[H-].[Na+].I[CH:15]([CH2:17][CH3:18])[CH3:16].C(N1C=C(I)C(C2SC=CC=2)=N1)(CC)C>CN(C)C=O.CC(OC)(C)C.O>[CH:15]([N:4]1[C:3]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)=[C:2]([I:1])[CH:6]=[N:5]1)([CH2:17][CH3:18])[CH3:16]

참가 물질

8

반응물 4

HCID 105592-IodobutaneHCID 24758Sodium hydrideHCID 672603351-sec-butyl-4-iodo-3-(2-thienyl)-1H-pyrazoleHCID 178506561HCID 178506561, 화합물

생성물 1

HCID 672606651-sec-butyl-4-iodo-5-(2-thienyl)-1H-pyrazole수율 88%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 15413tert-Butyl methyl ether용매

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온도
0 °C

실험 절차

To a solution of 4-iodo-3-(2-thienyl)-1H-pyrazole (7.1 mmol) in 57 mL dry N,N-dimethylformamide under argon atmosphere at 0° C. was added sodium hydride (8.5 mmol, 60% dispersion in mineral oil) in portions. The reaction mixture was stirred at 0° C. for 15 min, then 2-iodobutane (10.6 mmol) was added dropwise. After 14 h at room temperature, water and MTBE were added to the reaction mixture. The phases were separated and the aqueous phase was extracted with MTBE. The combined organic extracts were successively washed with water and brine, dried over MgSO4, filtered and concentrated to afford 2.7 g of a mixture of 1-sec-butyl-4-iodo-3-(2-thienyl)-1H-pyrazole and 1-sec-butyl-4-iodo-5-(2-thienyl)-1H-pyrazole (80:20; 88% yield). The mixture was purified by chromatography on silica gel (toluene:ethyl acetate 100:0 to 0:100 and cyclohexane:toluene 100:0 to 0:100) to afford 1.16 g 1-sec-butyl-4-iodo-3-(2-thienyl)-1H-pyrazole (48% yield) and 71 mg of 1-sec-butyl-4-iodo-5-(2-thienyl)-1H-pyrazole (3% yield).

후처리

  1. waitAfter 14 h at room temperature
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with MTBE
  4. washThe combined organic extracts were successively washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ba8d8d0749da45dfbde70340c95f5e55
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08685974B2

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