Reaktion #1136068

Reaktionsgleichung

Compound R

Ethyl 6-ethynyl-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

4-bromo-2-(trifluoromethyl)pyridine

triethylamine

→

title compound

Ausbeute 45.1%

Ethyl 1-(4-fluorophenyl)-4-oxo-6-((2-(trifluoromethyl)pyridin-4-yl)ethynyl)-1,4-dihydroquinoline-3-carboxylate

Ausbeute 45.1%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe vial was capped
2. 2
   workup.WAITplaced in microwave reactor at 150° C. for fifteen minutes
3. 3
   FiltrationThe reaction was filtered over Celite®
4. 4
   Waschenwashed very well with a 5% MeOH in DCM solution
5. 5
   Einengenconcentrated to dryness
6. 6
   SonstigePurification by reverse phase HPLC

Vorschrift

Compound R (20 mg, 0.06 mmol), 4-bromo-2-(trifluoromethyl)pyridine (16.2 mg, 0.07 mmol), CuI (1.1 mg, 0.006 mmol), triethylamine (25 μL, 0.18 mmol), PdCl2(PPh3)2 (2.7 mg, 0.003 mmol), and DMF (600 μL) were added to a small microwave vial. The vial was capped and placed in microwave reactor at 150° C. for fifteen minutes. The reaction was filtered over Celite®, washed very well with a 5% MeOH in DCM solution and concentrated to dryness. Purification by reverse phase HPLC afforded 13 mg (45%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.84 (d, J=4.96 Hz, 1H), 8.52-8.5 (m, 2H), 8.17 (s, 1H), 7.93 (d, J=5.04 Hz, 1H), 7.87 (dd, J=8.8 Hz, 1H), 7.81-7.77 (m, 2H), 7.55 (t, J=8.64, 8.68 Hz, 2H), 7.07 (d, J=8.8 Hz, 1H), 4.24 (q, J=7.04, 7.08 Hz, 2H), 1.28 (t, J=7.12, 7.08 Hz, 3H); ES-MS [M+1]+: 481.2.

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