Iodine → HCID 25114169, compound

HRID 557275Notes

Reaction equation

HRID 557275 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[O:10][N:9]=[C:8]([CH2:11][C:12]2[CH:25]=[CH:24][C:15]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[CH:14][CH:13]=2)[CH:7]=1)CCC.[I:34]I.S([O-])([O-])(=O)=S.[Na+].[Na+].C(OCC)(=O)C>O1CCCC1>[I:34][C:6]1[O:10][N:9]=[C:8]([CH2:11][C:12]2[CH:25]=[CH:24][C:15]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[CH:14][CH:13]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 807IodineHCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 25114168HCID 25114168, compound

Product 1

HCID 25114169HCID 25114169, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-(5-tributylstannyl-isoxazol-3-yl methyl)-benzyloxy)-pyridine (5.1 g) in tetrahydrofuran (15 mL) was added iodine (2.5 g) at 0° C. This mixture was stirred for 20 minutes at this temperature. To this mixture was added an aqueous solution of 10% sodium thiosulfate and ethyl acetate. The organic layer thereof was separated, washed with saturated sodium chloride water, dried over anhydrous magnesium sulfate and then filtered. The filtrate thereof was concentrated, and the residue thereof was purified by silica gel column chromatography (heptane:ethyl acetate=10:1 to 4:1) to obtain the title compound (2.4 g).

Workup

  1. customThe organic layer thereof was separated
  2. washwashed with saturated sodium chloride water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate thereof was concentrated
  6. customthe residue thereof was purified by silica gel column chromatography (heptane:ethyl acetate=10:1 to 4:1)

Sources & evidence

ORD record
ord-280b889dd32e46d29c7fe990cd47439b
Source dataset
uspto-grants-2011_11
Patent number
US08058444B2

Reaction notes

Loading…