Sodium Iodide → HCID 57752713, compound

HRID 226112Notes

Reaction equation

HRID 226112 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[C:25]([CH:26](O)[CH3:27])[C:20]=4[O:19][C:18]=3[CH3:29])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].CCN(CC)CC.CS(Cl)(=O)=O.[Na+].[I-]>C(Cl)Cl>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[C:25]([CH:26]=[CH2:27])[C:20]=4[O:19][C:18]=3[CH3:29])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57752602HCID 57752602, compound

Product 1

HCID 57752713HCID 57752713, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-{3-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-benzofuran-7-yl}-ethanol (0.64 g, 1.63 mmol) is dissolved in CH2Cl2 (20 mL), treated with Et3N (0.27 mL, 1.95 mmol) and MsCl (0.14 mL, 1.79 mmol). The reaction is stirred at rt overnight. It is diluted with CH2Cl2 (40 mL), washed with H2O (2×40 mL); dried with Na2SO4; filtered and concentrated. The resulting crude material is dissolved in acetone (20 mL), refluxed with NaI (0.31 g, 2.04 mmol) overnight. The organic solvent is removed in vacuo, the residue is taken up with H2O (30 mL) and extracted with EtOAc (2×30 mL); the combined organic layers are dried with Na2SO4; filtered and concentrated. Purification of the crude material by chromatography gives the title compound (0.28 g, 0.75 mmol, 46%). 1H NMR (CDCl3): δ. 0.90 (t, J=7.0 Hz, 3H), 0.91 (t, J=7.0 Hz, 3H), 1.76-1.95 (m, 4H), 2.45 (s, 3H), 2.46 (s, 3H), 2.47 (s, 3H), 3.32-3.44 (m, 1H), 5.52 (dd, J=11.5, 1.3 Hz, 1H), 6.23 (dd, J=19.0, 1.3 Hz, 1H), 6.68 (s, 1H), 7.04 (dd, J=19.0, 11.5 Hz, 1H), 7.15 (d, J=1.3 Hz, 1H), 7.16 (s, 1H), 7.29 (t, J=4.8 Hz, 1H) ppm. ES-MS (m/z): calcd for C24H27N3O (M+H)+: 374.5. found: 374.2.

Workup

  1. washwashed with H2O (2×40 mL)
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe resulting crude material is dissolved in acetone (20 mL)
  6. customThe organic solvent is removed in vacuo
  7. extractionextracted with EtOAc (2×30 mL)
  8. dry with materialthe combined organic layers are dried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification of the crude material by chromatography

Sources & evidence

ORD record
ord-dc63666642214bf0ada2d3dfb5eecd54
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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