N-Iodosuccinimide → 8-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine

HRID 226007노트

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HRID 226007 반응식
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([CH:13]=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].C1C(=O)N([I:24])C(=O)C1>C(#N)C.C(OCC)(=O)C>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([I:24])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

참가 물질

5

반응물 2

HCID 120273N-IodosuccinimideHCID 688412672,6-Dimethyl-8-(pentan-3-yl)imidazo[1,2-b]pyridazine

생성물 1

HCID 577526818-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

In nitrogen-purged flask is added 5.1 g (0.023 moles) of 8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine in 50 ml dry acetonitrile. Cool to 0° C. and add 5.54 g (0.025 moles) of NIS dissolved in 90 ml dry acetonitrile. Allow bath to come to room temperature and the reaction to stir overnight. Evaporate solvents, take up in ethyl acetate and wash two times with 50% aqueous solution of sodium sulfate then brine. Dry over sodium sulfate, filter and evaporate to a residue. Triturate in small amount of acetonitrile and filter solid. Repeat several times to obtain the title compound as light tan solid weighing 7.29 g (0.021 moles, 91.3%). 1H-NMR (DMSO-d6): δ 6.96 (s, 1H); 3.0-3.3 (m, 1H); 2.51 (s, 3H); 2.35 (s, 3H); 1.71-1.80 (m, 4H); 0.71 (t, J=7.48 hz, 6H) ppm. MS/ES+=344 (100%, M+1).

후처리

  1. customIn nitrogen-purged flask
  2. customto come to room temperature
  3. customthe reaction
  4. washwash two times with 50% aqueous solution of sodium sulfate
  5. dry with materialDry over sodium sulfate
  6. filtrationfilter
  7. customevaporate to a residue
  8. customTriturate in small amount of acetonitrile
  9. filtrationfilter solid

출처 및 근거

ORD 기록
ord-ccbbb5f2e8c34ddda9a511301a2acb80
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557103B2

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