Iodine → 3-(4-Fluorophenylethynyl)-5-iodopyridine

HRID 606866Notes

Reaction equation

HRID 606866 reaction equation
C([Mg]Cl)(C)C.Br[C:7]1[CH:8]=[N:9][CH:10]=[C:11]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:12]=1.[I:22]I.O>O1CCCC1.C(OCC)C>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]#[C:13][C:11]2[CH:10]=[N:9][CH:8]=[C:7]([I:22])[CH:12]=2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 807IodineHCID 962WaterHCID 670476153-Bromo-5-(4-fluorophenylethynyl)-pyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 670479393-(4-Fluorophenylethynyl)-5-iodopyridineYield 53%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Add a 2 M solution of isopropylmagnesium chloride in tetrahydrofuran (81 mL, 161.7 mmol) to a solution of 3-bromo-5-(4-fluorophenylethynyl)-pyridine, (prepared essentially as described in PREPARATION 24), (40.5 g, 147 mmol) in anhydrous tetrahydrofuran (400 mL) at room temperature under nitrogen. Stir for 1 h, add a solution of iodine (41 g, 161.7 mmol) in anhydrous tetrahydrofuran (250 mL) and stir for an additional 16 h. Add water (200 mL) to the reaction mixture, dilute with diethyl ether (400 mL) and separate the layers. Sequentially wash the organic layer with a 10% aqueous solution of sodium thiosulfate (150 mL), water (200 mL) and an aqueous saturated solution of sodium chloride, dry (magnesium sulfate), filter and concentrate. Purify by silica gel chromatography, eluting with 15:1 hexanes:ethyl acetate, to give the title compound as a pale yellow solid (25.4 g, 53%).

Workup

  1. custom(prepared essentially
  2. stirringstir for an additional 16 h
  3. customseparate the layers
  4. washSequentially wash the organic layer with a 10% aqueous solution of sodium thiosulfate (150 mL), water (200 mL)
  5. dry with materialan aqueous saturated solution of sodium chloride, dry (magnesium sulfate)
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify by silica gel chromatography
  9. washeluting with 15:1 hexanes

Sources & evidence

ORD record
ord-70013ddd89754d0ca0331ce785d2c31e
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

Loading…