Diisopropylethylamine → 3-(1-(Tert-butyldimethylsilyloxy)vinyl)-2-(pyridin-2-ylethynyl)pyridine

HRID 1402708Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]#[C:8][C:9]1[C:14]([C:15](=[O:17])[CH3:16])=[CH:13][CH:12]=[CH:11][N:10]=1.CCN(C(C)C)C(C)C.[Si:27](OS(C(F)(F)F)(=O)=O)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]>C(Cl)Cl>[Si:27]([O:17][C:15]([C:14]1[C:9]([C:8]#[C:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:10][CH:11]=[CH:12][CH:13]=1)=[CH2:16])([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 0 °C

Procedure

455 mg 1-(2-(pyridin-2-ylethynyl)pyridin-3-yl)ethanone was dissolved in 10 mL DCM, 1.069 mL of DIPEA was added, the solution was cooled 0° C. and 1.42 mL of tert-butyldimethylsilyltrifluormethansulfonate added slowly. The mixture was stirred 30 min at 0° C., warmed to 25° C. and filtrated over a plug of silica (cyclohexane/ethylacetate 1:1+small amount of TEA) to yield 1.025 g 3-(1-(tert-butyldimethylsilyloxy)vinyl)-2-(pyridin-2-ylethynyl)pyridine as oil. Analysis: HPLC-MS: Rt=1.59 min (method E) m+H=337.

Workup

temperaturewarmed to 25° C.
filtrationfiltrated over a plug of silica (cyclohexane/ethylacetate 1:1+small amount of TEA)

Sources & evidence

ORD record: ord-fbc27dcd088c4ae895178efc2fc8fe94
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912173B2

Reaction notes

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