Cesium carbonate → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-(3-methyl-benzo[b]thiophen-2-yl)-imidazo[1,2-b]pyridazine

HRID 226010

Reaction equation

HRID 226010 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13](I)=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].[CH3:18][C:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[S:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN(C=O)C>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:20]3[S:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:19]=3[CH3:18])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 738173-Methylbenzo[b]thiopheneHCID 577526818-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine

Product 1

HCID 577526258-(1-Ethyl-propyl)-2,6-dimethyl-3-(3-methyl-benzo[b]thiophen-2-yl)-imidazo[1,2-b]pyridazineYield 80%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.145 mmol), 3-methyl-benzothiophene (7.25 mmol), Pd2 dba3 (0.0072 mmol), triphenylphosphine (0.029 mmol), and cesium carbonate (0.29 mmol) in previously degassed DMF (0.5 ml) is added to a pressure tube with a stirring bar. Mixture is degassed for 30 min. After heating for 16 h at 130° C., the reaction mixture is cooled, diluted with diethylether and washed with saturated aqueous ammonium chloride solution. The organic layer is dried over anhydrous magnesium sulfate, filtered, and the solvent is removed in vacuo. The residue is purified by silica gel column chromatography using mixtures of hexane-ethyl acetate as eluent to give the title compound (80%).

Workup

  1. additionis added to a pressure tube with a stirring bar
  2. customMixture is degassed for 30 min
  3. temperaturethe reaction mixture is cooled
  4. additiondiluted with diethylether
  5. washwashed with saturated aqueous ammonium chloride solution
  6. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent is removed in vacuo
  9. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-43ac9d937e5c4f608cbb04b3b604d3a8
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Linked notes

Loading…