N-Iodosuccinimide → HCID 68839933, compound

HRID 1432657Notes

Reaction equation

HRID 1432657 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:18][CH:19]=[CH:20][C:21]=3[O:22][CH3:23])=[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:31])C(=O)C1>CC#N>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:18][C:19]([I:31])=[CH:20][C:21]=3[O:22][CH3:23])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 57932986HCID 57932986, compound

Product 1

HCID 68839933HCID 68839933, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 8-(1-ethyl-propyl)-3-(3-methoxy-thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.75 g, 2.28 mmol) and CH3CN (10 mL) is added NIS (0.54 g, 2.39 mmol). The solution is stirred overnight, concentrated, diluted with EtOAc (30 mL), washed with water (30 mL), sat. NH4Cl (30 mL), 20% (NaHSO3) (30 mL), brine (30 mL), dried over MgSO4, filtered and concentrated. The residue is purified by ISCO column chromatography (15%-20% EtOAc/hexane gradient) furnish the title compound (0.91 g, 2.00 mmol, 88%). 1H NMR (CDCl3) δ 0.85 (t, J=7.5 Hz, 6H), 1.71-1.89 (m, 4H), 2.46 (s, 3H), 2.52 (s, 3H), 3.25-3.35 (m, 1H), 3.83 (s, 3H), 6.64 (s, 1H), 7.12 (s, 1H). LC/MS (m/z): calcd. for C18H22IN3OS (M+H)+: 456.4; found: 456.0.

Workup

  1. concentrationconcentrated
  2. additiondiluted with EtOAc (30 mL)
  3. washwashed with water (30 mL), sat. NH4Cl (30 mL), 20% (NaHSO3) (30 mL), brine (30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by ISCO column chromatography (15%-20% EtOAc/hexane gradient)

Sources & evidence

ORD record
ord-70cd8e4ded6b45729caca18bc5a46bb0
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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