N-Iodosuccinimide → 4-iodo-1-methyl-5-(4-methylphenyl)-1H-pyrazole

HRID 1498005Notes

Reaction equation

[I:1]N1C(=O)CCC1=O.[CH3:9][N:10]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:13][CH:12]=[N:11]1>C(#N)C>[I:1][C:13]1[CH:12]=[N:11][N:10]([CH3:9])[C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 85 °C

Procedure

N-Iodosuccinimide (95%, 756 mg, 3.19 mmol) was added to a solution of 1-methyl-5-(4-methylphenyl)-1H-pyrazole (500 mg, 2.90 mmol) in acetonitrile (15 mL), and the reaction was allowed to stir for 1 hour at 85° C. Removal of solvent in vacuo provided a residue, which was chromatographed on silica gel (Gradient: 20% to 50% ethyl acetate in heptane) to provide the product as a brown oil. Yield: 630 mg, 2.11 mmol, 73%. LCMS m/z 299.2 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.44 (br s, 3H), 3.83 (s, 3H), 7.26-7.33 (m, 4H), 7.57 (s, 1H).

Workup

customRemoval of solvent in vacuo
customprovided a residue, which
customwas chromatographed on silica gel (Gradient: 20% to 50% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-9f02acb3c1fe48ba9c420082f232b47c
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09200000B2

Reaction notes

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