Iodine → HCID 25114169, compound

HRID 1894686Notes

Reaction equation

HRID 1894686 reaction equation
O1CCCC1.C([Sn](CCCC)(CCCC)[C:11]1[O:15][N:14]=[C:13]([CH2:16][C:17]2[CH:30]=[CH:29][C:20]([CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[CH:19][CH:18]=2)[CH:12]=1)CCC.[I:39]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)(=O)C>[I:39][C:11]1[O:15][N:14]=[C:13]([CH2:16][C:17]2[CH:30]=[CH:29][C:20]([CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[CH:19][CH:18]=2)[CH:12]=1

Participants

6

Reactant 4

HCID 807IodineHCID 8028TetrahydrofuranHCID 24477Sodium ThiosulfateHCID 25114168HCID 25114168, compound

Product 1

HCID 25114169HCID 25114169, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a tetrahydrofuran solution (15 mL) of 2-(4-(5-tri-n-butylstannyl-isoxazol-3-ylmethyl)-benzyloxy)-pyridine (5.1 g) described in Manufacturing Example 1-8-1 was added iodine (2.5 g) at 0° C. This mixture was stirred at this temperature for 20 minutes. A 10% sodium thiosulfate aqueous solution and ethyl acetate were added to this mixture. The organic layer was separated, washed with saturated saline, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated, and the residue 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 was separated
  2. washwashed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=10:1 to 4:1)

Sources & evidence

ORD record
ord-82d95be981254478b30de3c280c47d74
Source dataset
uspto-grants-2013_08
Patent number
US08513287B2

Reaction notes

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