Nitrogen → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-(4-methyl-oxazol-5-yl)-imidazo[1,2-b]pyridazine

HRID 1432595Notes

Reaction equation

HRID 1432595 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[N:20]=[CH:21][O:22][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].N#N>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].O.CN(C=O)C>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:23]3[O:22][CH:21]=[N:20][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

9

Reactant 5

HCID 947NitrogenHCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 696634-MethyloxazoleHCID 577526818-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine

Product 1

HCID 579329208-(1-Ethyl-propyl)-2,6-dimethyl-3-(4-methyl-oxazol-5-yl)-imidazo[1,2-b]pyridazineYield 39.2%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

686 mg of 8-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (2.0 mmol), 830 mg of 4-methyl-oxazole. (10 mmol), 105 mg of triphenylphosphine (0.4 mmol) and 1.30 g of cesium carbonate (4.0 mmol) are placed into tube with 10 ml of dry DMF. N2 gas is bubbled in for 20 min and 92 mg of Pd2 dba3 (0.1 mmol) is added. The tube is sealed and heated at 130° C. overnight. After being cooled to room temperature, water and CHCl2 are added to the mixture. The CHCl2 layer is separated, washed with sat. NaCl, dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane:AcOEt=5:1) to give 234 mg of the title product. Yield 39%. mass spectrum (m/e): 299 (M+1). 1H-NMR (CDCl3): 8.06 (s, 1H), 6.75 (s, 1H), 3.34 (m, 1H), 2.56 (s, 3H), 2.50 (s, 3H), 2.29 (s, 3H), 1.86 (m, 4H), 0.90 (t, J=7.4 Hz, 6H).

Workup

  1. additionis added
  2. customThe tube is sealed
  3. temperatureAfter being cooled to room temperature
  4. customThe CHCl2 layer is separated
  5. washwashed with sat. NaCl
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-91f245a169854643946962e41de57644
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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