反応 #2286380

反応方程式

methyl-(2-pyridin-3-yl-4-trifluoromethyl-thiazol-5-yl)-carbamic acid tert-butyl ester

trifluoroacetic acid

→

desired product

収率 81.0%

methyl-(2-pyridin-3-yl-4-trifluoromethyl-thiazol-5-yl)-amine

収率 81.0%

溶媒

DCE

反応条件

後処理

1. 1
   その他The solvents were removed under reduced pressure
2. 2
   workup.DISSOLUTIONthe resulting residue was re-dissolved in DCE
3. 3
   その他The biphasic mixture was separated
4. 4
   抽出the aqueous layer was extracted three times with DCE
5. 5
   乾燥dried over MgSO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated to dryness under reduced pressure
8. 8
   その他The crude product was purified by silica gel column chromatography (0 to 100% ethyl acetate/hexanes)

実験手順

To a solution of DCE (4 mL) was added methyl-(2-pyridin-3-yl-4-trifluoromethyl-thiazol-5-yl)-carbamic acid tert-butyl ester (0.616 g, 1.7 mmol) and trifluoroacetic acid (4 mL) and the mixture was stirred for 15 min. The solvents were removed under reduced pressure and the resulting residue was re-dissolved in DCE and aqueous saturated NaHCO3. The biphasic mixture was separated and the aqueous layer was extracted three times with DCE. The organic extracts were combined, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. The crude product was purified by silica gel column chromatography (0 to 100% ethyl acetate/hexanes) to give the desired product as an off-white solid (0.357 g, 80%): mp 152-157° C.; 1H NMR (300 MHz, CDCl3) δ 8.95 (d, J=2.3 Hz, 1H), 8.57 (dd, J=4.9, 1.7 Hz, 1H), 8.11 (dt, J=8.2, 2.3 Hz, 1H), 7.23 (ddd, J=7.9, 4.9, 0.7 Hz, 1H), 4.83 (br s, 1H), 3.05 (d, J=4.9 Hz, 3H); ESIMS m/z 260 (M+1), m/z 257.9 (M−1).

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