反応 #422400

反応方程式

1-(5-bromo-3-phenoxypyridin-2-yl)thiourea

methyl 5-bromo-2-methoxy-2-methyl-4-oxopentanoate

→

title compound

収率 65.8%

methyl 3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)-2-methoxy-2-methylpropanoate

収率 65.8%

溶媒

THF

反応条件

後処理

1. 1
   その他The solvent was evaporated
2. 2
   workup.DISSOLUTIONthe residue was dissolved in chloroform
3. 3
   洗浄washed with diluted sodium bicarbonate solution twice
4. 4
   乾燥dried over magnesium sulfate
5. 5
   ろ過filtered
6. 6
   その他evaporated
7. 7
   その他The resulting solid was purified by chromatography on silica gel
8. 8
   洗浄eluted with 10-15% ethyl acetate/hexane

実験手順

In a 125 mL round-bottom flask, 1-(5-bromo-3-phenoxypyridin-2-yl)thiourea (0.50 g, 1.54 mmol) (prepared as described in Example 10, Steps A-D) and methyl 5-bromo-2-methoxy-2-methyl-4-oxopentanoate (0.586 g, 2.31 mmol) were dissolved in dry THF (25 mL), heated to 50° C. and agitated overnight. The solvent was evaporated and the residue was dissolved in chloroform and washed with diluted sodium bicarbonate solution twice, dried over magnesium sulfate, filtered and evaporated. The resulting solid was purified by chromatography on silica gel, eluted with 10-15% ethyl acetate/hexane to give the title compound (0.485 g, 65.7% yield) as yellow solid. 1H NMR (CDCl3) δ 1.46 (s, 3H), 3.12 (s, 2H), 3.34 (s, 3H), 3.73 (s, 3H), 6.58 (s, 1H), 7.06-7.45 (m, 6H), 8.11 (s, 1H), 8.64 (bs, 1H).

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