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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
ノート
印刷プレビュー

反応式

HRID 226096 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 3007855
Zincchloride
触媒
HCID 962Water溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ba71d9cb7a5f4195b1e5ddf93c141fec
出典データセット
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07557103B2

反応ノート

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