Water → HCID 67352950, compound

HRID 1895889Notes

Reaction equation

HRID 1895889 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][CH:17]=2)[CH:6]=[C:7](C2C=CC=CC=2)[CH:8]=1.C1C(=O)N([I:25])C(=O)C1.C(OCC)(=O)C.O>C(#N)C>[I:25][C:17]1[CH:16]=[N:15][N:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=12

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 120273N-IodosuccinimideHCID 671856604-Methoxy-6-phenylpyrazolo[1,5-a]pyridine

Product 1

HCID 67352950HCID 67352950, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-methoxy-6-phenylpyrazolo[1,5-a]pyridine (17, 200 mg, 0.892 mmol) and NIS (241 mg, 1.070 mmol) were dissolved in acetonitrile (20 mL) and stirred at room temperature for 1 hour. The reaction was then poured into ethyl acetate and water, extracted organics, washed 1N NaOH and brine, dried with magnesium sulfate, filtered, and concentrated to give a white solid. This was purified by column chromatography (0-30% ethyl acetate in hexanes, linear gradient) and to yield 3-iodo-4-methoxypyrazolo[1,5-a]pyridine (18, 310 mg, 0.885 mmol, 99% yield). MS APCI: [M+H]+ m/z 351.2.

Workup

  1. extractionextracted organics
  2. washwashed 1N NaOH and brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a white solid
  7. customThis was purified by column chromatography (0-30% ethyl acetate in hexanes, linear gradient)

Sources & evidence

ORD record
ord-98e22db9ea61443d87856fdf3ea2d356
Source dataset
uspto-grants-2013_08
Patent number
US08518911B2

Reaction notes

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