反応 #2286390

反応方程式

tert-butyl 2-(5-fluoropyridin-3-yl)thiazol-5-ylcarbamate

N-iodosuccinimide

→

tert-butyl 2-(5-fluoropyridin-3-yl)-4-iodothiazol-5-ylcarbamate

収率 84.1%

溶媒

acetonitrile

ethyl acetate

water

反応条件

後処理

1. 1
   その他The organic phase was separated
2. 2
   洗浄rinsed with brine
3. 3
   乾燥dried over MgSO4
4. 4
   濃縮concentrated in vacuo
5. 5
   その他to give a dark solid
6. 6
   洗浄eluting with 10% ether in hexanes (600 mL)

実験手順

To a solution of tert-butyl 2-(5-fluoropyridin-3-yl)thiazol-5-ylcarbamate (1.50 g, 5.08 mmol) in acetonitrile (50 mL) at 0° C. was added N-iodosuccinimide (2.40 g, 10.67 mmol). The mixture was stirred at 0° C. for 5 min and diluted with ethyl acetate and water. The organic phase was separated and rinsed with brine, dried over MgSO4 and concentrated in vacuo to give a dark solid. This solid was passed through a bed of silica gel (100 g) eluting with 10% ether in hexanes (600 mL) to give tert-butyl 2-(5-fluoropyridin-3-yl)-4-iodothiazol-5-ylcarbamate as a pale yellow solid (1.80 g, 84% yield): mp 148-149° C.; 1H NMR (300 MHz, CDCl3) δ 8.87 (t, J=1.5 Hz, 1H), 8.47 (d, J=2.7 Hz, 1H), 7.93 (ddd, J=9.0, 2.5, 1.9 Hz, 1H), 7.08 (s, 1H), 1.57 (s, 9H). ESIMS m/z 422.1 (M+1), 420.2 (M−1),

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