Iodine → HCID 87705647, compound

HRID 1296692Notes

Reaction equation

HRID 1296692 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:35])[O:10][C:11]3[C:16]([C:17]=2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][NH:29]4)=[CH:21][CH:20]=2)=[CH:15][CH:14]=[C:13]([OH:34])[CH:12]=3)=[CH:4][CH:3]=1.[OH-].[NH4+].[I:38]I>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9](=[O:35])[O:10][C:11]3[C:16]([C:17]=2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][NH:29]4)=[CH:21][CH:20]=2)=[CH:15][CH:14]=[C:13]([OH:34])[C:12]=3[I:38])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14923Ammonium HydroxideHCID 87706061HCID 87706061, compound

Product 1

HCID 87705647HCID 87705647, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution containing 3-(4-chlorophenyl)-7-hydroxy-4-{(4-(2-piperidylethoxy)phenyl)methyl}-2H-chromen-2-one (0.500 g.) in methanol (10 mL) was added ammonium hydroxide (3 mL) and elemental iodine (0.259 g.). The reaction mixture was allowed to stir at room temperature for 10 minutes. The solvent was removed under reduced pressure. The resulting solid was extracted with methylene chloride (3×) and water. The organic layers were combined and dried over magnesium sulfate. The magnesium sulfate was filtered, and the solvent was removed under reduced pressure to afford a yellow solid. The solid was purified via preparative HPLC (20–50% acetonitrile/water, 20 mL/min.) to afford the title compound (0.290 g., 46% yield). 1H-NMR (CDCl3) δ 7.34 (dd, 3H), 7.20 (d, 2H), 6.92 (d, 2H), 6.84 (d, 1H), 6.75 (d, 2H), 4.13 (t, 2H), 3.97 (s, 2H), 2.84 (t, 2H), 2.61 (bs, 3H), 1.643 (m, 4H), 1.46 (m, 2H), 1.24 (m, 1H). MS (m/z) 616 (M+1)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionThe resulting solid was extracted with methylene chloride (3×) and water
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe magnesium sulfate was filtered
  5. customthe solvent was removed under reduced pressure
  6. customto afford a yellow solid
  7. customThe solid was purified via preparative HPLC (20–50% acetonitrile/water, 20 mL/min.)

Sources & evidence

ORD record
ord-c5fd5c637ebb4fc8aef591fa53d7ec6b
Source dataset
uspto-grants-2007_07
Patent number
US07247646B2

Reaction notes

Loading…