Acetic Acid → 3-Iodo-6-(phenylethynyl)pyridazine

HRID 629242Notes

Reaction equation

HRID 629242 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:7]=1.[I-:16].[Na+].C(O)(=O)C.S(=O)(=O)(O)O>C(#N)C.C(OCC)(=O)C.O>[I:16][C:2]1[N:3]=[N:4][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 5238Sodium IodideHCID 126802603-Chloro-6-(phenylethynyl)pyridazine

Product 1

HCID 575167733-Iodo-6-(phenylethynyl)pyridazineYield 58%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 100 mg (0.466 mmol) of 3-chloro-6-(phenylethynyl)pyridazine in 5 ml of acetonitrile were added sodium iodide (209 mg, 1.4 mmol, 3 equiv.), acetic acid (56 mg, 53.3 ml, 0.93 mmol, 2 equiv.), and 95% sulfuric acid (4.6 mg, 2.5 ml, 0.47 mmol, 1 equiv.). The orange solution was stirred for 8 hours at 70° C. and then left to cool overnight. After standard workup with ethyl acetate/water, the residue was adsorbed onto 4 g of silicagel and purified by flash chromatography over a 20 g silicagel column over a heptane to 50% ethyl acetate in heptane gradient to yield 82 mg (58% yield) of the title compound as a crystalline light yellow solid, MS: m/e=307.1 (M+H+).

Workup

  1. waitleft
  2. temperatureto cool overnight
  3. custompurified by flash chromatography over a 20 g silicagel column over a heptane to 50% ethyl acetate in heptane gradient

Sources & evidence

ORD record
ord-5a400e785db04073bb5d7ab8142e27c1
Source dataset
uspto-grants-2016_04
Patent number
US09315498B2

Reaction notes

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