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

HRID 514555Notes

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 lg, 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-a6433fa392044945a796a52658906b99
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09107916B2

Reaction notes

Loading…