Potassium Iodide → 3-Iodo-6-methoxy-2-(trifluoromethyl)pyridine

HRID 1297288Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6](N)=[CH:5][CH:4]=1.N([O-])=O.[Na+].[I-:18].[K+]>OS(O)(=O)=O.O>[I:18][C:6]1[C:7]([C:9]([F:12])([F:11])[F:10])=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

6-methoxy-2-(trifluoromethyl)pyridin-3-amine (1 g) was dissolved in H2SO4 (3 ml) and a dropwise addition of sodium nitrite (718 mg) in H2O (3 ml) was made to reaction mixture at 0° C. After 2 hour of stirring at 0° C., it was raised to room temperature. Potassium iodide (1.73 g) in H2O (3 ml) was added to the reaction mixture in a drop-wise fashion. It was heated to 60° C. for 3 hour. It was extracted with ethyl acetate, washed with sodium thiosulfate solution (Sat.), dried (MgSO4), filtered and concentrated. The flash column chromatography (SiO2, 1˜5% EtOAc in heptane) gave the title compounds (3.47 g, 67%). 1H NMR (CDCl3) δ 3.97, 6.68; 8.08; 19F NMR (CDCl3) δ 66.16; IR (liq.) 2478 (w), 2364 (w), 2230 (w), 2173 (w), 2026 (w), 1585 (s), 1471 (s), 1422 (s), 1396 (s), 1338 (s), 1280 (s), 1238 (s), 1200 (s), 1180, 1140 (s) cm−1 Anal. Calcd for C7H5F3INO: C, 27.75; H, 1.66; N, 4.62; F, 18.81. Found: C, 27.93; H, 1.80; N, 4.62.

Workup

customwas made to reaction mixture at 0° C
temperatureit was raised to room temperature
temperatureIt was heated to 60° C. for 3 hour
extractionIt was extracted with ethyl acetate
washwashed with sodium thiosulfate solution (Sat.)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-5cbeef9153314d818680c4c5ba88af6c
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250418B2

Reaction notes

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