Iodoethane → 2-(2,5-Dimethyl-pyrrol-1-yl)-6-propyl-pyridine

HRID 2197696Notes

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+].[CH3:16][CH:17]([N-]C(C)C)C.C(I)C>C1COCC1>[CH3:7][C:4]1[N:3]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH2:16][CH3:17])[N:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: -30 °C

Procedure

A solution of the product from Example 2a (7.53 g, 40.0 mmol) in 30 mL of dry THF was added dropwise with stirring to a solution of LDA (42.4 mmol) in 30 mL of dry THF at −30° C. Stirred at −30° C. for 30 min. Added EtI (3.42 mL, 42.0 mmol) in 20 mL of dry THF dropwise with stirring for 30 min then warmed to room temperature. After 2 h quenched by pouring into saturated NaCl solution and extracted with ether. Dried over MgSO4, filtered and concentrated under vacuum giving the title compound. The product was purified by silica gel column chromatography eluting with EtOAc/hexane to give the title compound (5.21 g, 60%).

Workup

temperaturethen warmed to room temperature
customAfter 2 h quenched
additionby pouring into saturated NaCl solution
extractionextracted with ether
dry with materialDried over MgSO4
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-54ccb51e2ba74ae58ac3698404a40e06
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338605B2

Reaction notes

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