Cesium carbonate → 3-(3,5-Dimethyl isoxazol-4-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

HRID 1432720Notes

Reaction equation

HRID 1432720 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([CH:13]=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].Br[C:18]1[C:19]([CH3:24])=[N:20][O:21][C:22]=1[CH3:23].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:24][C:19]1[C:18]([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:22]([CH3:23])[O:21][N:20]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 3184214-Bromo-3,5-dimethyl-1,2-oxazoleHCID 688412672,6-Dimethyl-8-(pentan-3-yl)imidazo[1,2-b]pyridazine

Product 1

HCID 579329513-(3,5-Dimethyl isoxazol-4-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazineYield 23.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Using the procedure analogous to Example 242, from 8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (200 mg, 0.90 mmol), 4-bromo-3,5-dimethyl isoxazole (Alfa, 320 mg, 1.8 mmol), cesium carbonate (880 mg, 2.70 mmol) and PdCl2(PPh3)2 (25 mg) in DMF (5 ml), heated at 130 for 4 hrs, then overnight at ambient temperature gives the title compound (65 mg, 23% yield). ES-MS (m/z): calc'd for C18H24N4O: 312.4; found 313.2 (M+H)+. 1H NMR (400 mHz, CDCl3): δ 6.68 (s, 1H), 3.32 (m, 1H), 2.50 (s, 3H), 2.39 (s, 3H), 2.33 (s, 3H), 2.19 (s, 3H), 1.82 (m, 4H), 0.87 (m, 6H).

Sources & evidence

ORD record
ord-3a4b3232dcca4ca49d47e16805a7035f
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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