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

HRID 226116

Reaktionsgleichung

Reaktionsgleichung von HRID 226116
[CH3:1][CH2:2][CH2-:3].[Mg+2].[Br-].CON(C)[C:9]([C:11]1[C:12]2[N:13]([C:18]([C:22]3[S:26][C:25]4[CH:27]=[CH:28][C:29]([F:31])=[CH:30][C:24]=4[C:23]=3[CH3:32])=[C:19]([CH3:21])[N:20]=2)[N:14]=[C:15]([CH3:17])[CH:16]=1)=[O:10]>C1COCC1>[F:31][C:29]1[CH:28]=[CH:27][C:25]2[S:26][C:22]([C:18]3[N:13]4[N:14]=[C:15]([CH3:17])[CH:16]=[C:11]([C:9](=[O:10])[CH2:1][CH2:2][CH3:3])[C:12]4=[N:20][C:19]=3[CH3:21])=[C:23]([CH3:32])[C:24]=2[CH:30]=1

Komponenten

4

Edukt 2

HCID 101916BromopropylmagnesiumHCID 866210453-(5-Fluoro-3-methyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine-8-carboxylic acid methoxy-methyl-amide

Produkt 1

HCID 688590651-[3-(5-Fluoro-3-methyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-8-yl]-butan-1-oneAusbeute 463,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-Propylmagnesium bromide (0.303 g, 2.06 mmol) is added dropwise to a solution of 3-(5-fluoro-3-methyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine-8-carboxylic acid methoxy-methyl-amide (0.21 g, 0.52 mmol) in THF (5 mL) at 0° C. The reaction is stirred at room temperature overnight. The mixture is quenched with H2O, extracted with CH2Cl2, dried over sodium sulfate, filtered, and concentrated to dryness. The crude is purified through an ISCO column (5-10% EtOAc/Hexane) to give the title compound (0.92 g, 42%). 1H NMR (CDCl3): δ 7.8 (dd, J=4.8, 8.5 Hz, 1H), 7.5 (dd, J=2.5, 9.7 Hz, 1H), 7.4 (s, 1H), 7.2 (m, 1H), 3.6 (t, J=5.7, 2H), 2.6 (s, 3H), 2.55 (s, 3H), 2.3 (s, 3H), 1.9 (m, 2H), 1.1 (t, J=7.5, 3H) ppm. MS (m/e): 382 (M+1).

Aufarbeitung

  1. customThe mixture is quenched with H2O
  2. extractionextracted with CH2Cl2
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude is purified through an ISCO column (5-10% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-6fda92cc3b3b47ec977a3e89d2c84380
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557103B2

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