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Hydrochloric Acid → 8-(1-Ethyl-propyl)-3-(5-fluoro-3-methyl-benzofuran-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

HRID 226096
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HRID 226096 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([CH3:10])[C:6]=2[CH:11]=1.[Li]CCCC.[CH2:17]([CH:19]([C:22]1[C:23]2[N:24]([C:29](I)=[C:30]([CH3:32])[N:31]=2)[N:25]=[C:26]([CH3:28])[CH:27]=1)[CH2:20][CH3:21])[CH3:18].Cl>[Cl-].[Cl-].[Zn+2].O.C1COCC1>[CH2:17]([CH:19]([C:22]1[C:23]2[N:24]([C:29]([C:8]3[O:9][C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:11][C:6]=4[C:7]=3[CH3:10])=[C:30]([CH3:32])[N:31]=2)[N:25]=[C:26]([CH3:28])[CH:27]=1)[CH2:20][CH3:21])[CH3:18]
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참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 116798475-Fluoro-3-methylbenzofuranHCID 577526818-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazineHCID 178418339Butyllithium

생성물 1

HCID 577526538-(1-Ethyl-propyl)-3-(5-fluoro-3-methyl-benzofuran-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine수율 54%

시약·촉매·용매 3

HCID 3007855
Zincchloride
촉매
HCID 962Water용매
HCID 8028Tetrahydrofuran용매

실험 절차

A THF solution (6 mL) of 5-fluoro-3-methyl-benzofuran (187.0 mg, 1.25 mmol) is cooled to −78° C. under N2 then treated with nBuLi (1.6 M in hexane, 1.0 mL, 1.6 mmol). After 10 min at −78° C., ZnCl2 (Aldrich, 0.5 M in THF, 3.0 mL, 1.5 mmol) is added. The resulting mixture is warmed to room temperature and treated with 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (212.4 mg, 0.62 mmol) and PdCl2(dppf)-CH2Cl2 complex (Aldrich, 60 mg, 0.073 mmol). The mixture is heated to 65° C. for 18 hours, then poured into H2O, acidified with 1 N HCl then extracted with ethyl acetate. The organic extract is ished with aq. brine, dried over Na2SO4, filtered, and concentrated. The crude product is purified by chromatography using hexane-ethyl acetate gradient (100% hexane to 20% ethyl acetate in hexane) to give the title compound as a solid (121.7 mg, 54% yield).

후처리

  1. temperatureThe mixture is heated to 65° C. for 18 hours
  2. extractionthen extracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by chromatography

출처 및 근거

ORD 기록
ord-ba71d9cb7a5f4195b1e5ddf93c141fec
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07557103B2

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