Bromopropylmagnesium → 4-[3-(5-Fluoro-3-methyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-8-yl]-heptan-4-ol

HRID 226117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 226117
[CH3:1][CH2:2][CH2-:3].[Mg+2].[Br-].[F:6][C:7]1[CH:32]=[CH:31][C:10]2[S:11][C:12]([C:15]3[N:19]4[N:20]=[C:21]([CH3:29])[CH:22]=[C:23]([C:24](=[O:28])[CH2:25][CH2:26][CH3:27])[C:18]4=[N:17][C:16]=3[CH3:30])=[C:13]([CH3:14])[C:9]=2[CH:8]=1>C1COCC1>[F:6][C:7]1[CH:32]=[CH:31][C:10]2[S:11][C:12]([C:15]3[N:19]4[N:20]=[C:21]([CH3:29])[CH:22]=[C:23]([C:24]([OH:28])([CH2:1][CH2:2][CH3:3])[CH2:25][CH2:26][CH3:27])[C:18]4=[N:17][C:16]=3[CH3:30])=[C:13]([CH3:14])[C:9]=2[CH:8]=1

Komponenten

4

Edukt 2

HCID 101916BromopropylmagnesiumHCID 688590651-[3-(5-Fluoro-3-methyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-8-yl]-butan-1-one

Produkt 1

HCID 577526054-[3-(5-Fluoro-3-methyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-8-yl]-heptan-4-olAusbeute 24,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-Propylmagnesium bromide (0.601 g, 4.09 mmol) is added dropwise to a solution of 1-[3-(5-fluoro-3-methyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-8-yl]-butan-1-one (1.08 g, 2.72 mmol) in THF (27 mL) at 0° C. The reaction is stirred at room temperature overnight. The mixture is quenched with ammonium chloride, extracted with ethylacetate, dried over sodium sulfate, filtered, and concentrated to dryness. The crude is purified by ISCO (5% EtOAc/Hexane) to give the title compound (280 mg, 24%). 1H NMR (CDCl3): δ 7.8 (dd, J=4.8, 8.5 Hz, 1H), 7.5 (dd, J=2.5, 9.7 Hz, 1H), 7.2 (m, 1H), 6.7 (s, 1H), 6.4 (s, 1H), 2.6 (s, 3H), 2.5 (s, 3H), 2.3 (s, 3H), 2.0 (m, 3H), 1.5 (m, 1H), 1.3 (m, 4H), 0.9 (t, J=7.3, 6H) ppm. Mass spectrum (m/e): 426 (M+1).

Aufarbeitung

  1. customThe mixture is quenched with ammonium chloride
  2. extractionextracted with ethylacetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude is purified by ISCO (5% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-8293ec1e86804ceb9c52eb4835f4370c
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557103B2

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