8-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-(2-methyl-thieno[3,2-c]pyridin-3-yl)-imidazo[1,2-b]pyridazine

HRID 226068Notes

Reaction equation

Br[C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[CH3:11].[CH2:12]([CH:14]([C:17]1[C:18]2[N:19]([C:24](I)=[C:25]([CH3:27])[N:26]=2)[N:20]=[C:21]([CH3:23])[CH:22]=1)[CH2:15][CH3:16])[CH3:13]>C1COCC1.[Zn]>[CH2:12]([CH:14]([C:17]1[C:18]2[N:19]([C:24]([C:2]3[C:6]4[CH:7]=[N:8][CH:9]=[CH:10][C:5]=4[S:4][C:3]=3[CH3:11])=[C:25]([CH3:27])[N:26]=2)[N:20]=[C:21]([CH3:23])[CH:22]=1)[CH2:15][CH3:16])[CH3:13]

Participants

Conditions

Temperature: 100 °C

Procedure

225 mg of 3-Bromo-2-methyl-thieno[3,2-c]pyridine (0.98 mmol) is placed into the vial with 2.14 ml of Reiki Zn, suspension in THF (1.50 mmol) and capped and heated at 100° C. for 2 h. The excess Zinc is allowed to settle down and the solution is transferred to the vial containing 200 mg of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.58 mmol) and 41 mg of PdCl2(pddf) (0.05 mmol) in 3 ml of dry THF. The vial is capped with a Teflon cap and heated at 80° C. for 2 days. The reaction mixture is quenched by sat. NH4Cl and extracted by CH2Cl2, dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane:AcOEt:2 M NH3 in MeOH=20:4:1) to give 12.8 mg of the title compound. Yield 4%. Mass spectrum (m/e): 365 (M+1); 1H-NMR (CDCl3): 8.54 (m, 1H), 8.46 (m, 1H), 7.80 (m, 1H), 6.74 (s, 1H), 3.41 (m, 1H), 2.51 (s, 3H), 2.47 (s, 3H), 2.44 (s, 3H), 1.89 (m, 4H), 0.94 (m, 6H) ppm.

Workup

customcapped
customcap
temperatureheated at 80° C. for 2 days
customThe reaction mixture is quenched by sat. NH4Cl
extractionextracted by CH2Cl2
dry with materialdried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-d3ae4a09a7c34f6db3dc47981dc726c5
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557103B2

Reaction notes

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