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

HRID 226030Notes

Reaction equation

HRID 226030 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([CH:16]=[C:17]([CH3:19])[N:18]=2)[N:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].C1C(=O)N([I:27])C(=O)C1>CC#N.CCOC(C)=O>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:16]([I:27])=[C:17]([CH3:19])[N:18]=2)[N:9]=[C:10]([C:12]([F:13])([F:15])[F:14])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 688564838-(1-Ethyl-propyl)-2-methyl-6-trifluoromethyl-imidazo[1,2-b]pyridazine

Product 1

HCID 688564568-(1-Ethyl-propyl)-3-iodo-2-methyl-6-trifluoromethyl-imidazo[1,2-b]pyridazineYield 98%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 8-(1-ethyl-propyl)-2-methyl-6-trifluoromethyl-imidazo[1,2-b]pyridazine (0.18 g, 0.67 mmol) in CH3CN (5 mL) is treated with NIS (0.18 g, 0.80 mmol), and stirred at rt overnight. It is diluted with EtOAc (50 mL), washed with 5% Na2SO3 (2×25 mL); dried (Na2SO4), filtered and concentrated to give the title compound (0.26 g, 0.65 mmol, 98%). 1H NMR (CDCl3): δ 0.85 (t, J=7.0 Hz, 6H), 1.79-1.92 (m, 4H), 2.59 (s, 3H), 3.30-3.43 (m, 1H), 7.09 (s, 1H). ES-MS (m/z): calcd for C13H15F31N3 (M+H)+: 398.2. found: 398.1.

Workup

  1. washwashed with 5% Na2SO3 (2×25 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9c29c5a295354a5c9d049a49934ccd07
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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