Cesium carbonate → HCID 57752717, compound

HRID 226092Notes

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][N:19]1[CH:27]=[C:26]2[C:21]([CH:22]=[CH:23][CH:24]=[CH:25]2)=[N:20]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:18][N:19]1[C:27]([C:13]2[N:8]3[N:9]=[C:10]([CH3:12])[CH:11]=[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[C:7]3=[N:15][C:14]=2[CH3:16])=[C:26]2[C:21]([CH:22]=[CH:23][CH:24]=[CH:25]2)=[N:20]1

Participants

Conditions

Temperature: 100 °C

Procedure

8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (300 mg, 0.87 mmol), 2-methyl-2H-indazole (ref. J. Org. Chem. 2003, 68, 4093-4095, 230 mg, 1.76 mmol) and cesium carbonate (570 mg, 1.75 mmol) stirred in DMF (5 ml) and degassed by bubbling a stream of nitrogen through the mixture. PdCl2(PPh3)2 added and the mixture heated to 100° C. overnight. The mixture is added to water and extracted twice with ether. The combined organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated. The crude product is purified by chromatography using a hexane-ethyl acetate gradient (100% hexane to 50% ethyl acetate in hexane) to give the title compound (85 mg, 28% yield).

Workup

customdegassed
customby bubbling a stream of nitrogen through the mixture
additionPdCl2(PPh3)2 added
additionThe mixture is added to water
extractionextracted twice with ether
washThe combined organic extracts are washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product is purified by chromatography

Sources & evidence

ORD record: ord-40938ba1f71d4106a46adfe4f26ff92f
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557103B2

Reaction notes

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