N-bromobutanimide → 3-(5-Bromo-3-methoxy-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

HRID 1432654Notes

Reaction equation

HRID 1432654 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:18][CH:19]=[CH:20][C:21]=3[O:22][CH3:23])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].C1C(=O)N([Br:31])C(=O)C1>C(Cl)Cl>[Br:31][C:19]1[S:18][C:17]([C:13]2[N:8]3[N:9]=[C:10]([CH3:12])[CH:11]=[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[C:7]3=[N:15][C:14]=2[CH3:16])=[C:21]([O:22][CH3:23])[CH:20]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57932986HCID 57932986, compound

Product 1

HCID 579329853-(5-Bromo-3-methoxy-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazineYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-(1-ethyl-propyl)-3-(3-methoxy-thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.78 g, 2.37 mmol) and CH2Cl2 (10 mL) is added NBS (0.44 g, 2.49 mmol). The solution is stirred for 1 hour, washed with water (3×10 mL), concentrated and purified by ISCO column chromatography (5%-15% EtOAc/hexane gradient) to furnish the title compound (0.87 g, 2.13 mmol, 90%). 1H NMR (CDCl3) δ 0.85 (t, J=7.5 Hz, 6H), 1.71-1.89 (m, 4H), 2.46 (s, 3H), 2.52 (s, 3H), 3.25-3.35 (m, 1H), 3.82 (s, 3H), 6.65 (s, 1H), 6.97 (s, 1H). LC/MS (m/z): calcd. for C18H22BrN3OS (M+H)+: 408.1; found: 408.3.

Workup

  1. washwashed with water (3×10 mL)
  2. concentrationconcentrated
  3. custompurified by ISCO column chromatography (5%-15% EtOAc/hexane gradient)

Sources & evidence

ORD record
ord-213891dc01c047cca373d531b4267ee6
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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