Dichloromethane → 3-(5-Bromo-2-methyl-furan-3-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

HRID 1432694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1432694
C(Cl)Cl.[CH2:4]([CH:6]([C:9]1[C:10]2[N:11]([C:16]([C:20]3[CH:24]=[CH:23][O:22][C:21]=3[CH3:25])=[C:17]([CH3:19])[N:18]=2)[N:12]=[C:13]([CH3:15])[CH:14]=1)[CH2:7][CH3:8])[CH3:5].[Br:26]N1C(=O)CCC1=O>O>[Br:26][C:23]1[O:22][C:21]([CH3:25])=[C:20]([C:16]2[N:11]3[N:12]=[C:13]([CH3:15])[CH:14]=[C:9]([CH:6]([CH2:7][CH3:8])[CH2:4][CH3:5])[C:10]3=[N:18][C:17]=2[CH3:19])[CH:24]=1

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 579329758-(1-Ethyl-propyl)-2,6-dimethyl-3-(2-methyl-furan-3-yl)-imidazo[1,2-b]pyridazine

Produkt 1

HCID 579330743-(5-Bromo-2-methyl-furan-3-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A CH2Cl2 solution (2 mL) of 8-(1-ethyl-propyl)-2,6-dimethyl-3-(2-methyl-furan-3-yl)-imidazo[1,2-b]pyridazine (42.3 mg, 0.14 mmol) under a CaSO4 drying tube is treated with N-bromosuccinimide (27.6 mg, 0.16 mg). After 30 minutes the reaction mixture is poured into H2O (25 mL) and extracted into CH2Cl2 (2×25 mL). The combined organic extracts are washed with sat. NaCl, dried over Na2SO4, filtered, and concentrated. The crude product is purified by chromatography using hexane-ethyl acetate gradient (100% hexane to 12% ethyl acetate in hexane) to elute the title product (36.9 mg, 70% yield) as a white solid. ES-MS (m/z): calc'd for C18H22BrN3O: 375.1. found 376.3 (M+H). 1H NMR (400 mHz, CDCl3): δ 6.67 (s, 1H), 6.50 (s, 1H), 3.33 (m, 1H), 2.53 (s, 3H), 2.44 (s, 3H), 2.29 (s, 3H), 1.90-1.73 (m, 4H), 0.86 (t, J=7.3 Hz, 6H).

Aufarbeitung

  1. extractionextracted into CH2Cl2 (2×25 mL)
  2. washThe combined organic extracts are washed with sat. NaCl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5a1bc94fe86243d0849ecf76ec13fe25
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612067B2

Notizen zur Reaktion

Wird geladen…