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Iodine → 6-Chloro-3-(1-(6-fluoro-1-methyl-1H-indazol-5-yl)ethyl)imidazo[1,2-b]pyridazine

HRID 456146
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HRID 456146 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][C:22]=3[F:23])[N:19]([CH3:24])[N:18]=[CH:17]4)(O)[CH3:12])=[CH:9][N:10]=2)[N:7]=1.II.[PH2](=O)O>CC(O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][C:22]=3[F:23])[N:19]([CH3:24])[N:18]=[CH:17]4)[CH3:12])=[CH:9][N:10]=2)[N:7]=1
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참가 물질

5

반응물 3

HCID 807IodineHCID 4124402Phosphinic AcidHCID 581475401-(6-Chloroimidazo[1,2-b]pyridazin-3-yl)-1-(6-fluoro-1-methyl-1H-indazol-5-yl)ethanol

생성물 1

HCID 581475176-Chloro-3-(1-(6-fluoro-1-methyl-1H-indazol-5-yl)ethyl)imidazo[1,2-b]pyridazine수율 85.8%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
120 °C

실험 절차

A mixture of 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)-1-(6-fluoro-1-methyl-1H-indazol-5-yl)ethanol (1.1 g, 3.18 mmol), diiodine (2.019 g, 7.95 mmol), and phosphinic acid (0.840 g, 12.73 mmol) in HOAc (10 ml) was heated to 120° C. for 5 h. After cooling to rt, the reaction mixture was concentrated in vacuo. The residue was taken with water and adjusted its pH tp 8 with aqueous NaOH. The mixture was extracted with DCM, dried over Na2SO4 and concentrated to give a residue, which was purified with silica gel column chromatography (MeOH:EA) to give 6-chloro-3-(1-(6-fluoro-1-methyl-1H-indazol-5-yl)ethyl)imidazo[1,2-b]pyridazine (900 mg 60%). LCMS (method B): [MH]+=330, tR=2.59 min.

후처리

  1. temperatureAfter cooling to rt
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. extractionThe mixture was extracted with DCM
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give a residue, which
  7. customwas purified with silica gel column chromatography (MeOH:EA)

출처 및 근거

ORD 기록
ord-cdfbbd7a232d4c05bdd33cd90e3c3575
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08497368B2

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