Methyl iodide → 2-(2,5-Dimethyl-1H-pyrrol-1-yl)-6-ethylpyridine

HRID 883845Notes

Reaction equation

[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[Li][CH2:16]CCC.CI>C1COCC1>[CH3:7][C:4]1[N:3]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH3:16])[N:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: -30 °C

Procedure

To a solution of 2-(2,5-Dimethyl-pyrrol-1-yl)-6-methyl-pyridine (6.82 g, 36.6 mmol) in 75 mL of dry THF cooled to −40° C. under a N2 atmosphere was added dropwise n-BuLi as a 2.5M solution in hexanes (16 mL, 40 mmol). The resulting solution was stirred at low temperature for thirty minutes then treated with CH3I (2.4 mL, 38.6 mmol). On completion of the addition the mixture was allowed to warm to −30° C. and after 20 min to room temperature. The reaction was subsequently quenched by pouring into brine solution, the product isolated by extraction with EtOAc. Dried over MgSO4, filtered and concentration under vacuum. Purified by silica gel column chromatography eluting with EtOAc/hexane gave the title compound (4.42 g, 60%).

Workup

additionOn completion of the addition the mixture
customThe reaction was subsequently quenched
additionby pouring into brine solution
customthe product isolated by extraction with EtOAc
dry with materialDried over MgSO4
filtrationfiltered
concentrationconcentration under vacuum
customPurified by silica gel column chromatography
washeluting with EtOAc/hexane

Sources & evidence

ORD record: ord-7d5ccdac43b14078baf27068cc9ae15b
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236950B2

Reaction notes

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