Water → 2-[4-[2-[Tert-butyl(dimethyl)silyl]oxyethyl]pyrazol-1-yl]pyridine-4-carbonitrile

HRID 878711Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.[C:10]([Si:14]([CH3:24])([CH3:23])[O:15][CH2:16][CH2:17][C:18]1[CH:19]=[N:20][NH:21][CH:22]=1)([CH3:13])([CH3:12])[CH3:11].O>CN1C(=O)CCC1>[Si:14]([O:15][CH2:16][CH2:17][C:18]1[CH:22]=[N:21][N:20]([C:2]2[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=2)[CH:19]=1)([C:10]([CH3:11])([CH3:13])[CH3:12])([CH3:23])[CH3:24]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-chloropyridine-4-carbonitrile (1.38 g, 10 mmol), tert-butyl-dimethyl-[2-(1H-pyrazol-4-yl)ethoxy]silane (2.48 1 g, 11 mmol) in NMP (30 mL) was stirred for 5 hr at 150° C. Then the reaction mixture was cooled to room temperature and poured into water and extracted with ethyl acetate three times. Organic extracts collected and washed with water twice, brine and dried with anhydrous Na2SO4. It was then concentrated and purified by flash column chromatograph to give the title compound (1.2 g, 36%). [M+H] Calc'd for C17H24N4O3Si, 329; Found, 329.

Workup

temperatureThen the reaction mixture was cooled to room temperature
extractionextracted with ethyl acetate three times
customOrganic extracts collected
washwashed with water twice
dry with materialbrine and dried with anhydrous Na2SO4
concentrationIt was then concentrated
custompurified by flash column chromatograph

Sources & evidence

ORD record: ord-4fa1273860d54928b47cbb5841ab319d
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987461B2

Reaction notes

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