8-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine → HCID 57933035, compound

HRID 1432602Notes

Reaction equation

HRID 1432602 reaction equation
Br[C:2]1[S:6][C:5]([CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)=[CH:4][C:3]=1[CH3:13].C([Li])CCC.[CH2:19]([CH:21]([C:24]1[C:25]2[N:26]([C:31](I)=[C:32]([CH3:34])[N:33]=2)[N:27]=[C:28]([CH3:30])[CH:29]=1)[CH2:22][CH3:23])[CH3:20]>[Cl-].[Cl-].[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:19]([CH:21]([C:24]1[C:25]2[N:26]([C:31]([C:2]3[S:6][C:5]([CH:7]4[CH2:12][CH2:11][O:10][CH2:9][CH2:8]4)=[CH:4][C:3]=3[CH3:13])=[C:32]([CH3:34])[N:33]=2)[N:27]=[C:28]([CH3:30])[CH:29]=1)[CH2:22][CH3:23])[CH3:20]

Participants

6

Reactant 3

HCID 577526818-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazineHCID 68840392HCID 68840392, compoundHCID 178418339Butyllithium

Product 1

HCID 57933035HCID 57933035, compoundYield 11.5%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

Using a procedure similar to Example 25, 4-(5-bromo-4-methyl-thiophen-2-yl)-tetrahydropyran (0.83 g, 3.19 mmol), 1.56 M n-Bu-Li (2.04 mL, 3.19 mmol), ZnCl2 (6.4 mL, 3.19 mmol), 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.50 g, 1.56 mmol) and Pd(PPh3)4 (0.092 g, 0.008 mmol) furnish the title compound (0.072 g, 0.18 mmol, 11%). Spectrum identical to that from Method A.

Sources & evidence

ORD record
ord-a43ac98f024b41159f3ab9efa6ad7106
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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