Acetic Acid → 2-Ethyl-3-iodopyrazolo[1,5-a]pyridine

HRID 1478692Notes

Reaction equation

HRID 1478692 reaction equation
[CH2:1]([C:3]1[CH:11]=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2].C(O)(=O)C.[I:16]N1C(=O)CCC1=O>>[CH2:1]([C:3]1[C:11]([I:16])=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 120273N-IodosuccinimideHCID 161162612-Ethylpyrazolo[1,5-a]pyridine

Product 1

HCID 161149332-Ethyl-3-iodopyrazolo[1,5-a]pyridineYield 93%

Procedure

2-Ethylpyrazolo[1,5-a]pyridine (4.1 g, 22 mmol) was stirred in acetic acid (2.6 g, 18 mmol) and N-iodosuccinimide (8 g, 40 mmol) was added in portions over 5 hrs. The mixture was evaporated and purified on silica gel with ethyl acetate in hexanes (0-15%) to give the desired compound (4.5 g, 93%). LCMS for C9H10IN2 (M+H)+: m/z=273.1. 1H NMR (300 MHz, DMSO-d6): δ 8.62 (m, 1 H), 7.40 (m, 1 H), 7.27 (m, 1 H), 6.82 (m, 1 H), 2.72 (m, 2 H), 1.22 (m, 3 H).

Workup

  1. customThe mixture was evaporated
  2. custompurified on silica gel with ethyl acetate in hexanes (0-15%)

Sources & evidence

ORD record
ord-3b6fdeb72ae74ab58779a22af6eaaa43
Source dataset
uspto-grants-2016_08
Patent number
US09403847B2

Reaction notes

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