Reaktion #2488682

Reaktionsgleichung

potassium bis(trimethylsilyl)amide

toluene

Compound 7

methyl 3-chloro-5-(pyrimidin-5-yloxy)benzoate

HCl

2-Amino-4-fluoropyridine

→

title compound

Ausbeute 38.5%

3-chloro-N-(4-fluoropyridin-2-yl)-5-(pyrimidin-5-yloxy)benzamide

Ausbeute 38.5%

Lösungsmittel

THF

EtOAc

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction was stirred for 30 min
2. 2
   Waschenwashed with water
3. 3
   TrocknenThe organic layer was dried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigePurification by flash chromatography on silica gel

Vorschrift

2-Amino-4-fluoropyridine (254 mg, 2.27 mmol, 2.00 eq) was dissolved in THF (2.5 mL) in a flame-dried round bottom flask. A 0.5 M solution of potassium bis(trimethylsilyl)amide in toluene (4.76 mL, 2.27 mmol, 2.00 eq) was added dropwise and the reaction was stirred for 5 min. Compound 7 (300 mg, 1.13 mmol, 1.00 eq) was added as a solution in THF (2.5 mL) and the reaction was stirred for 30 min. The reaction was diluted with EtOAc, neutralized with 1N HCl and washed with water. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 150 mg (38%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 11.12 (s, 1H), 9.07 (s, 1H), 8.75 (s, 2H), 8.39 (d, J=3.0 Hz, 1H), 8.16 (dd, J=5.0, 4.2 Hz, 1H), 7.88 (t, J=1.6 Hz, 1H), 7.80 (td, J=8.7, 31. Hz, 1H), 7.68 (t, J=2.0 Hz, 1H), 7.58 (t, J=2.1 Hz, 1H); [M+1]+: 345.2

Quelle