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

HRID 1432622Notes

Reaction equation

HRID 1432622 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[N:11]2[N:12]=[C:13]([CH3:21])[CH:14]=[C:15]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[C:10]2=[N:9][C:8]=1[CH3:22].C1C(=O)N([Br:30])C(=O)C1>C(Cl)Cl>[Br:30][C:5]1[S:4][C:3]([C:7]2[N:11]3[N:12]=[C:13]([CH3:21])[CH:14]=[C:15]([CH:16]([CH2:17][CH3:18])[CH2:19][CH3:20])[C:10]3=[N:9][C:8]=2[CH3:22])=[C:2]([Cl:1])[CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 579329363-(3-Chloro-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

Product 1

HCID 579329223-(5-Bromo-3-chloro-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazineYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3-chloro-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine. (1.15 g, 3.44 mmol) and CH2Cl2 (12 mL) is added NBS (0.64 g, 3.62 mmol). The solution is stirred at ambient temperature overnight, washed with water (2×75 mL), brine (75 mL), dried over Na2SO4, filtered and concentrated to furnish the title compound (1.36 g, 3.29 mmol, 96%). 1H NMR (CDCl3), δ 0.88 (t, J=7.5 Hz, 6H), 1.74-1.92 (m, 4H), 2.49 (s, 3H), 2.53 (s, 3H), 3.26-3.36 (m, 1H), 6.70 (s, 1H), 7.07 (s, 1H). LC/MS (m/z): calcd. for C17H19BrClN3S (M+H)+: 412.1; found: 412.0.

Workup

  1. washwashed with water (2×75 mL), brine (75 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5332f48ab8fd42428f3eab38aca67503
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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