Iodine → N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-7-iodophenazine-1-carboxamide

HRID 2273654Notes

Reaction equation

HRID 2273654 reaction equation
[CH2:1]([N:3]([CH2:14][CH2:15][NH:16][C:17]([C:19]1[C:32]2[C:23](=[N:24][C:25]3[C:30]([N:31]=2)=[CH:29][CH:28]=[C:27]([Sn](CCCC)(CCCC)CCCC)[CH:26]=3)[CH:22]=[CH:21][CH:20]=1)=[O:18])[CH2:4][CH2:5][O:6][C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:2].[I:46]I.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([N:3]([CH2:14][CH2:15][NH:16][C:17]([C:19]1[C:32]2[C:23](=[N:24][C:25]3[C:30]([N:31]=2)=[CH:29][CH:28]=[C:27]([I:46])[CH:26]=3)[CH:22]=[CH:21][CH:20]=1)=[O:18])[CH2:4][CH2:5][O:6][C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 807IodineHCID 10340Sodium CarbonateHCID 52952477N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-7-(tributylstannyl)phenazine-1-carboxamide

Product 1

HCID 52952478N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-7-iodophenazine-1-carboxamideYield 54.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of compound 83 (270 mg, 0.37 mmol) in chloroform (7 mL), was added during 4 h, a solution of diiodine (192 mg, 0.76 mmol) in chloroform (14 mL), dropwise. The mixture was then stirred 14 h at room temperature before addition of an aqueous saturated sodium carbonate solution (40 mL). The solution was decanted and the organic layer was washed with a 5% aqueous sodium hydrogenosulfite solution (2×15 mL), dried on magnesium sulfate, filtered and evaporated under vacuum. The residue was chromatographed (Al2O3, AcOEt/cyclohexane, 7/3, v/v) to give compound 84 (112 mg, 0.20 mmol) as a yellow oil. Yield 54%; Rf (Al2O3, AcOEt/cyclohexane, 7/3, v/v) 0.68; IR (CCl4) ν 1119, 1189, 1246, 1286, 1458, 1509, 1649, 2800-3000, 3246 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.14 (t, 3H, J=7.1 Hz), 2.86 (m, 4H), 3.05 (t, 2H, J=5.5 Hz), 3.76 (q, 2H, J=5.5 Hz), 4.10 (t, 2H, J=5.5 Hz), 6.80 (dd, 1H, J=4.9, 7.9 Hz), 6.97 (m, 1H), 7.53 (m, 1H), 7.83 (dd, 1H, J=1.4, 9.2 Hz), 7.93 (m, 2H), 8.25 (dd, 1H, J=1.5, 8.7 Hz), 8.60 (se, 1H), 8.92 (dd, 1H, J=1.5, 7.2 Hz), 10.92 (m, 1H); ESI-MS m/z 560.0 [M+H]+.

Workup

  1. customThe solution was decanted
  2. washthe organic layer was washed with a 5% aqueous sodium hydrogenosulfite solution (2×15 mL)
  3. customdried on magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customThe residue was chromatographed (Al2O3, AcOEt/cyclohexane, 7/3

Sources & evidence

ORD record
ord-64d132a3350140f78e724a0737de62f3
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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