Reaktion #718095

Reaktionsgleichung

Hexachloroethane

(S)-1-Methyl-piperidine-2-carboxylic acid N′-(5-fluoro-pyridin-2-yl)-hydrazide

Intermediate 120a

triethylamine

triphenylphosphine

→

title compound

Ausbeute 42.0%

6-Fluoro-3-((S)-1-methyl-piperidin-2-yl)-[1,2,4]triazolo[4,3-a]pyridine

Ausbeute 42.0%

Lösungsmittel

methanol

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe cartridge was washed with MeOH
2. 2
   Waschenthe product eluted with 2M NH3 in MeOH
3. 3
   Einengenconcentrated in vacuo
4. 4
   SonstigeThe resultant residue was purified by FCC on silica

Vorschrift

Hexachloroethane (505 mg, 2.14 mmol) was added portionwise over 5 min at RT to a stirred mixture of Intermediate 120a (270 mg, 1.07 mmol), triethylamine (595 μL, 4.28 mmol) and triphenylphosphine (560 mg, 2.14 mmol) in THF (10 mL). The reaction mixture was stirred for 1.5 h and then diluted with methanol and loaded onto an SCX cartridge. The cartridge was washed with MeOH and the product eluted with 2M NH3 in MeOH and concentrated in vacuo. The resultant residue was purified by FCC on silica, using a gradient of 0-8% [2M NH3 in MeOH] in EtOAc to give the title compound (105 mg, 42%). 1H NMR (400 MHz, CDCl3): 1.34-1.51 (1H, m), 1.62-1.92 (5H, m), 2.00 (3H, s), 2.20 (1H, td, J=11.4, 3.7 Hz), 3.06 (1H, m), 3.87 (1H, dd, J=10.9, 3.3 Hz), 7.18 (1H, ddd, J=9.8, 7.6, 2.3 Hz), 7.71 (1H, ddd, J=9.9, 5.0, 0.7 Hz), 8.75-7.79 (1H, m).

Quelle