N-Iodosuccinimide → 8-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine

HRID 1432564Notes

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].C1C(=O)N([I:24])C(=O)C1>C(#N)C>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([I:24])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (5.1 g, 0.023 moles) and 50 mL of dry acetonitrile are added to a nitrogen purged flask and are cooled to 0° C. NIS (5.54 g, 0.025 moles) in 90 mL of dry acetonitrile is added. The bath is allowed to come to room temperature, and the reaction to stir overnight. The solvents are evaporated. The residue is taken up in ethyl acetate, washed two times with 50% aqueous solution of sodium thiosulfate and with brine. The organic layer is dried over sodium sulfate, filtered, and evaporated to a residue again. The crude product is triturated in a small amount of acetonitrile, and a solid is filter off. The trituration is repeated several times to obtain the title compound as a light tan solid weighing 7.29 g (0.021 moles, 91%). 1H-NMR (DMSO-d6), δ 6.96 (s, 1H); 3.0-3.3 (m, 1H); 2.51 (s, 3H); 2.35 (s, 3H); 1.71-1.80 (m, 4H); 0.71 (t, J=7.48 hz, 6H) ppm. MS/ES+=344 (100%, M+1).

Workup

customto come to room temperature
customthe reaction
customThe solvents are evaporated
washwashed two times with 50% aqueous solution of sodium thiosulfate
dry with materialThe organic layer is dried over sodium sulfate
filtrationfiltered
customevaporated to a residue again
customThe crude product is triturated in a small amount of acetonitrile
filtrationa solid is filter off

Sources & evidence

ORD record: ord-7d9f97dc59d64d00887b314208ec4aa6
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612067B2

Reaction notes

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