N-Iodosuccinimide → 2-(4-iodo-1-methyl-1H-pyrazol-5-yl)-5-(trifluoromethyl)pyridine

HRID 72710Notes

Reaction equation

[I:1]N1C(=O)CCC1=O.[CH3:9][N:10]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][N:16]=2)=[CH:13][CH:12]=[N:11]1>C(O)(=O)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]([C:21]([F:24])([F:22])[F:23])=[CH:17][N:16]=1

Participants

Conditions

Temperature: 70 °C

Procedure

N-Iodosuccinimide (95%, 427 mg, 1.80 mmol) was added to a mixture of 2-(1-methyl-1H-pyrazol-5-yl)-5-(trifluoromethyl)pyridine (C13) (390 mg, 1.72 mmol) and acetic acid (4 mL), and the reaction mixture was heated at 70° C. for 1 hour. The mixture was concentrated in vacuo and subjected to silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane) to afford the product as a white solid. Yield: 524 mg, 1.48 mmol, 86%. APCI m/z 353.8 (M+1). 1H NMR (400 MHz, CD3OD) δ 3.89 (s, 3H), 7.66 (s, 1H), 8.00 (br d, J=8 Hz, 1H), 8.17 (br dd, J=8, 2 Hz, 1H), 8.83 (br d, J=2 Hz, 1H).

Workup

concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-5f73ead2fb124b9bbaf38bf01016478a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829010B2

Reaction notes

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