Acetonitrile → 2-(4-iodo-5-methyl-1H-pyrazol-1-yl)pyridine

HRID 1253474Notes

Reaction equation

[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:5]=[CH:4][CH:3]=1.[I:13]N1C(=O)CCC1=O.C(#N)C>C(OCC)(=O)C>[I:13][C:3]1[CH:4]=[N:5][N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[C:2]=1[CH3:1]

Participants

Conditions

Temperature: 60 °C

Procedure

2-(5-methyl-1H-pyrazol-1-yl)pyridine (100 mg, 0.63 mmol) and N-iodosuccinimide (212 mg, 0.942 mmol) were added to acetonitrile (5 ml). The reaction mixture was heated to 60° C. After 1 hour, the reaction mixture was diluted with ethyl acetate, washed with 1N aqueous sodium hydroxide and brine, then dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/isohexane gradient) to afford 2-(4-iodo-5-methyl-1H-pyrazol-1-yl)pyridine. LRMS (ESI) calculated for C9H9IN3 [M+H]+, 286.0; found 286.0.

Workup

washwashed with 1N aqueous sodium hydroxide and brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel (ethyl acetate/isohexane gradient)

Sources & evidence

ORD record: ord-4609412c3d6b470e97dcc2a004a598e4
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455477B2

Reaction notes

Loading…