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

HRID 1432694Notes

Reaction equation

HRID 1432694 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-5a1bc94fe86243d0849ecf76ec13fe25
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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