Dichloromethane → 3-(5-Bromo-3,4-dimethyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

HRID 1432649Notes

Reaction equation

HRID 1432649 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8]1[N:12]2[N:13]=[C:14]([CH3:22])[CH:15]=[C:16]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:11]2=[N:10][C:9]=1[CH3:23].C(Cl)Cl.C1C(=O)N([Br:34])C(=O)C1>CCOCC>[Br:34][C:5]1[S:4][C:3]([C:8]2[N:12]3[N:13]=[C:14]([CH3:22])[CH:15]=[C:16]([CH:17]([CH2:18][CH3:19])[CH2:20][CH3:21])[C:11]3=[N:10][C:9]=2[CH3:23])=[C:2]([CH3:1])[C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 579330453-(3,4-Dimethyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

Product 1

HCID 579330573-(5-Bromo-3,4-dimethyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazineYield 80.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-(3,4-dimethyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.41 g, 1.25 mmol) and CH2Cl2 (30 mL) is added NBS (0.23 g, 1.32 mmol). The solution is stirred for 1 hour, diluted with Et2O (100 mL), washed with water (3×100 mL), brine (100 mL), dried (MgSO4) filtered and concentrated to furnish the title compound (0.41 g, 1.01 mmol, 80%). 1H NMR (CDCl3) δ 0.86 (t, J=7.4 Hz, 6H), 1.72-1.94 (m, 4H), 2.02 (s, 3H), 2.18 (s, 3H), 2.43 (s, 3H), 2.49 (s, 3H), 3.27-3.36 (m, 1H), 6.67 (s, 1H). LC/MS (m/z): calcd. for C19H24BrN3S (M+H)+: 407.4; found: 407.3.

Workup

  1. washwashed with water (3×100 mL), brine (100 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d0131704f1724f3aa6e467e0828f69a1
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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