2-Pyridinamine, N-(5-bromo-2-thiazolyl)- synthesis

6synthesis methods

Product Name:2-Pyridinamine, N-(5-bromo-2-thiazolyl)-
CAS Number:54670-78-9
Molecular formula:C8H6BrN3S
Molecular Weight:256.1223

96-50-4 Synthesis

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2-Pyridinamine, N-(5-bromo-2-thiazolyl)-

54670-78-9
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Yield:-

Reaction Conditions:

with water;sodium carbonate;tris-(dibenzylideneacetone)dipalladium⁽⁰⁾;4,5-bis(diphenylphosphino)-9,9-dimethylxanthene in toluene at 100; for 12 h;

Steps:

10

Example 10; (5-Bromo-thiazol-2-yiypyridin-2-yl-amme; A solution of 2-chloropyridine (0.34 g, 3.0 mmol), 2-aminothiazole (0.314 g,3.1 mmol), Na₂CO₃ (0.76 g, 7.2 mmol), Pd₂(dba)₃ (0.275 g, 0.3 mmol) and XantPhos (0.52 g, 0.9 mmol), H₂O (54 mg, 3.0 mmol) in toluene (25 ml) is heated at 100⁰C for 12 hours. The reaction mixture is filtered and then concentrated in vacuum. The residue is purified by column chromatography (silica gel, eluted with CH₂Cl₂:Me0H:NH₃ (7N, in MeOH) = EPO 20: 1 : 1) to give pyridin-2-yl-thiazol-2-yl-amine, which is then subjected to the standard bromination procedure to give the title compound as an off-white solid after HPLC purification: ¹H NMR (DMSOd₆) δ 6.95 (t, IH, J= 6.4 Hz), 7.03 (d, IH, J= 8.0 Hz), 7.44 (s, IH), 7.73 (t, IH, J = 6.4 Hz), 8.30 (d, IH, J = 3.6 Hz), 11.51 (s, IH); m/z [M⁺+.] 255.9.