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

HRID 1432573Notes

Reaction equation

HRID 1432573 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[CH3:22])=[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:30])C(=O)C1>C(Cl)Cl>[Br:30][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]([CH3:22])[CH:20]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 579330168-(1-Ethyl-propyl)-2,6-dimethyl-3-(3-methyl-thiophen-2-yl)-imidazo[1,2-b]pyridazine

Product 1

HCID 579329433-(5-Bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazineYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-(1-Ethyl-propyl)-2,6-dimethyl-3-(3-methyl-thiophen-2-yl)-imidazo[1,2-b]pyridazine (8.83 g, 28.17 mmol) and CH2Cl2 (90 mL) is added NBS (5.26 g, 29.58 mmol). The solution is stirred at ambient temperature for 2 hours. The solution is washed with water (3×75 mL), dried over MgSO4, filtered and concentrated to furnish the title compound (10.5 g, 26.76 mmol, 95%). 1H NMR (CDCl3), δ 0.87 (t, J=7.3 Hz, 6H), 1.73-1.93 (m, 4H), 2.09 (s, 3H), 2.44 (s, 3H), 2.51 (s, 3H), 3.26-3.36 (m, 1H), 6.68 (s, 1H), 6.98 (d, J=4.9 Hz, 1H) ppm. LC/MS (m/z): calcd. for C18H22BrN3S (M+H)+: 392.6; found: 392.1, 394.1.

Workup

  1. washThe solution is washed with water (3×75 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-342bff16b7a841daaff75bb5dc34ad5b
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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