2,6-Dibromopyridine → 2,6-Bis(2,2,6,6-tetramethylpiperidin-1-yl)pyridine

HRID 1779135Notes

Reaction equation

[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[NH:3]1.[K].C[Si]([N-][Si](C)(C)C)(C)C.Br[C:22]1[CH:27]=[CH:26][CH:25]=[C:24](Br)[N:23]=1>O1CCOCC1>[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[N:3]1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([N:3]2[C:4]([CH3:9])([CH3:8])[CH2:5][CH2:6][CH2:7][C:2]2([CH3:10])[CH3:1])[N:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a 1,4-dioxane solution (30 ml) of 2,2,6,6-tetramethylpiperidine (3.11 g, 22.0 mmol) and potassium-bis(trimethylsilyl)amide (4.39 g, 22.0 mmol)2 was added 2,6-dibromopyridine (2.37 g, 10.0 mmol). The reaction mixture was stirred vigorously at 100° C. overnight. After cooling down to room temperature, the reaction was quenched with water and extracted with diethyl ether/THF (1:1) mixtures. The combined extracts were washed with 1 M Na2CO3, dried over MgSO4, filtrated, and evaporated to dryness. The product was purified by flash chromatography on silica gel leading to colorless oil (Rf=0.5 in Ethylacetate:hexane=1:20, Yield=1.13 g (31.6%))

Workup

temperatureAfter cooling down to room temperature
customthe reaction was quenched with water
extractionextracted with diethyl ether/THF (1:1) mixtures
washThe combined extracts were washed with 1 M Na2CO3
dry with materialdried over MgSO4
filtrationfiltrated
customevaporated to dryness
customThe product was purified by flash chromatography on silica gel leading to colorless oil (Rf=0.5 in Ethylacetate:hexane=1:20, Yield=1.13 g (31.6%))

Sources & evidence

ORD record: ord-c3335102052743728ff378f989d3f90a
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09269912B2

Reaction notes

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