Methyl iodide → 2-(5-Nitro-3-(trifluoromethyl)pyridin-2-yl)propanenitrile

HRID 1050082Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].[N+:7]([C:10]1[CH:11]=[C:12]([C:19]([F:22])([F:21])[F:20])[C:13]([CH2:16][C:17]#[N:18])=[N:14][CH:15]=1)([O-:9])=[O:8].[CH3:23]I>CC#N>[N+:7]([C:10]1[CH:11]=[C:12]([C:19]([F:22])([F:20])[F:21])[C:13]([CH:16]([CH3:23])[C:17]#[N:18])=[N:14][CH:15]=1)([O-:9])=[O:8]

Participants

Conditions

Temperature: 40 °C

Procedure

K2CO3 (359 mg, 2.60 mmol) was added to a solution of 2-(5-nitro-3-(trifluoromethyl)pyridine-2-yl)acetonitrile (200 mg, 0.865 mmol) in MeCN (10 mL). MeI (3071 mg, 21.63 mmol) was added and the mixture was stirred at 40° C. for 10 h. Then the solution was concentrated and distributed between EA and saturated NaHCO3 solution. The combined organic extract was washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified by preparative TLC (PE/EA=5:1, Rf=0.5) to yield a light yellow solid of 2-(5-nitro-3-(trifluoromethyl)pyridin-2-yl)propanenitrile (73.6 mg, 0.300 mmol, 34.7% yield): 1H NMR (400 MHz, CDCl3) δ: 9.65 (d, J=2.2 Hz, 1H), 9.54 (d, J=2.2 Hz, 1H), 8.86 (d, J=2.2 Hz, 1H), 8.80 (d, J=2.0 Hz, 1H), 4.47 (q, J=7.1 Hz, 1H), 1.92 (s, 2H), 1.78 (d, J=7.1 Hz, 3H); ES-LCMS m/z 246.0 (M+H).

Workup

concentrationThen the solution was concentrated
extractionThe combined organic extract
washwas washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude material was purified by preparative TLC (PE/EA=5:1, Rf=0.5)

Sources & evidence

ORD record: ord-3f7b7f44b4894a4781300095c83d3987
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382238B2

Reaction notes

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