Dimethylformamide → Tert-butyl 2-(3-cyano-4-(2-methylpyridin-4-yl)phenyl)acetate

HRID 592155

Reaktionsgleichung

Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][C:3]=1[C:16]#[N:17].[CH3:18][C:19]1[CH:24]=[C:23]([Sn](CCCC)(CCCC)CCCC)[CH:22]=[CH:21][N:20]=1.CN(C=O)C>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:16]([C:3]1[CH:4]=[C:5]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:6]=[CH:7][C:2]=1[C:23]1[CH:22]=[CH:21][N:20]=[C:19]([CH3:18])[CH:24]=1)#[N:17]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

A mixture of tert-butyl 2-(4-chloro-3-cyanophenyl)acetate 111-7 (572 mg, 2.28 mmol), 2-methyl-4-(tributylstannyl)pyridine 111-8 (870 mg, 2.28 mmol) and Pd(PPh3)4 (220 mg, 0.2 mmol) and DMF (9 mL) was stirred at 120° C. for 10 hours under argon. After cooling to room temperature, the mixture was diluted with ethyl acetate, washed with saturated aqueous Na2S2O3 solution, water and brine, dried over Na2SO4, and concentrated to dryness by rotary evaporation. The crude was purified by silica gel flash chromatography, eluted with 5% methanol in dichloromethane to give tert-butyl 2-(3-cyano-4-(2-methylpyridin-4-yl)phenyl)acetate 111-9 as a yellow oil. MS m/z 309.2 (M+1).

Aufarbeitung

temperatureAfter cooling to room temperature
washwashed with saturated aqueous Na2S2O3 solution, water and brine
dry with materialdried over Na2SO4
concentrationconcentrated to dryness by rotary evaporation
customThe crude was purified by silica gel flash chromatography
washeluted with 5% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag: ord-2cab6c97868a4e3b91a2c368f2fa615c
Quelldatensatz: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09238646B2

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