Reaction #792222

Reaction equation

3-bromo-5-fluoropyridine

2-[6-(1,3-thiazol-2-yl)pyridin-2-yl]pyrimidine

2-[6-(1,3-Thiazol-2-yl)pyridin-2-yl]pyrimidine

cesium carbonate

→

2-{6-[5-(5-Fluoropyridin-3-yl)-1,3-thiazol-2-yl]pyridin-2-yl}pyrimidine

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   OtherFor work-up, the solvent was removed under reduced pressure
2. 2
   Otherthe residue was partitioned between ethyl acetate and water
3. 3
   Otherthe organic phase was dried
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   Otherpurified by column chromatography on silica gel

Procedure

Under argon, 88 mg (0.50 mmol) of 3-bromo-5-fluoropyridine, 120 mg (0.50 mmol) of 2-[6-(1,3-thiazol-2-yl)pyridin-2-yl]pyrimidine (cf. Example K, step 1), 326 mg (1.0 mmol) of cesium carbonate and 8 mg (0.01 mmol) of [(t-Bu)2P(OH)]2PdCl2 (“POPd”) in 10 ml of N,N-dimethylformamide were stirred at 120° C. for 16 hours. For work-up, the solvent was removed under reduced pressure, the residue was partitioned between ethyl acetate and water and the organic phase was dried, concentrated under reduced pressure and purified by column chromatography on silica gel RP-18 (mobile phase: water/acetonitrile/formic acid). This gave 11 mg (7% of theory) of 2-{6-[5-(5-fluoropyridin-3-yl)-1,3-thiazol-2-yl]pyridin-2-yl}pyrimidine.

Source