Reaktion #62204

Reaktionsgleichung

4-(1-methyl-4-(pyridin-4-yl)-1H-pyrazol-3-yl)phenol

1-(quinolin-2-yl)ethanol

triphenylphosphine

di-t-butyldiazodicarboxylate

NaOH

→

2-(1-(4-(1-methyl-4-(pyridin-4-yl)-1H-pyrazol-3-yl)phenoxy)ethyl)quinoline

Lösungsmittel

p-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture extracted with dichloromethane
2. 2
   SonstigeThe organic layers were dried
3. 3
   Einengenconcentrated
4. 4
   Sonstigethe residue purified on silica gel
5. 5
   Wascheneluted with a gradient of ethyl acetate-hexanes giving a yellow solid
6. 6
   SonstigeHPLC-MS (system 1) 4.73 min, m/e 407 (MH+)

Vorschrift

A mixture of 4-(1-methyl-4-(pyridin-4-yl)-1H-pyrazol-3-yl)phenol (75 mg, 0.30 mmol) and 1-(quinolin-2-yl)ethanol (78 mg, 0.45 mmol) in p-dioxane (2 mL) was treated sequentially at RT with triphenylphosphine (126 mg, 0.48 mmol) and di-t-butyldiazodicarboxylate (110 mg, 0.48 mmol) and the mixture was heated at 60° C. for 4 h. Aqueous 2N NaOH was added and the mixture extracted with dichloromethane. The organic layers were dried, concentrated, and the residue purified on silica gel eluted with a gradient of ethyl acetate-hexanes giving a yellow solid. Yield 36 mg, 29%. 1H NMR (CDCl3, 400 mHz) δ 8.40 (m, 2H), 8.10 (d, 1H, J=8.7 Hz), 8.06 (d, 1H, J=7.5 Hz), 7.77 (d, 1H, J=8.3 Hz), 7.71 (ddd, 1H), 7.55 (d, 1H, J=8.3 Hz), 7.53-7.49 (m, 2H), 7.25 (m, 2H), 7.10 (m, 2H), 6.88 (m, 2H), 5.59 (q, 1H, J=6.6 Hz), 3.91 (s, 3H), 1.75 (d, 3H, J=6.6 Hz). HPLC-MS (system 1) 4.73 min, m/e 407 (MH+).

Quelle