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

HRID 1432716Notes

Reaction equation

HRID 1432716 reaction equation
[Br:1][C:2]1[C:3]([Cl:24])=[C:4]([C:8]2[N:12]3[N:13]=[C:14]([CH3:22])[CH:15]=[C:16]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:11]3=[N:10][C:9]=2[CH3:23])[S:5][C:6]=1Br.[Li]CCCC>C1COCC1>[Br:1][C:2]1[C:3]([Cl:24])=[C:4]([C:8]2[N:12]3[N:13]=[C:14]([CH3:22])[CH:15]=[C:16]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:11]3=[N:10][C:9]=2[CH3:23])[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 579330503-(4,5-Dibromo-3-chloro-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazineHCID 178418339Butyllithium

Product 1

HCID 579330783-(4-Bromo-3-chloro-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazineYield 68.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using a procedure similar to Example 76, 3-(4,5-dibromo-3-chloro-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (1.83 g, 3.72 mmol), 1.6 M n-BuLi (2.56 mL, 4.09 mmol), and THF (30 mL) furnish the title compound (1.05 g, 2.54 mmol, 68%). 1H NMR (CDCl3) δ 0.87 (t, J=7.5 Hz, 6H), 1.73-1.92 (m, 4H), 2.48 (s, 3H), 2.51 (s, 3H), 3.27-3.36 (m, 1H), 6.71 (s, 1H), 7.55 (s, 1H). LC/MS (m/z): calcd. for C17H19BrClN3S (M+H)+: 412.0; found: 412.1.

Sources & evidence

ORD record
ord-e91e03c5cac749c4a39799195da720f1
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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