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

HRID 1428611Notes

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-ace0bd440cba4c0b957f998a7d443175
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937071B2

Reaction notes

Loading…