تفاعل #2286390

معادلة التفاعل

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

N-iodosuccinimide

→

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

المردود 84.1%

المذيبات

acetonitrile

ethyl acetate

water

ظروف التفاعل

المعالجة

1. 1
   أخرىThe organic phase was separated
2. 2
   غسيلrinsed with brine
3. 3
   تجفيفdried over MgSO4
4. 4
   تركيزconcentrated in vacuo
5. 5
   أخرىto give a dark solid
6. 6
   غسيلeluting with 10% ether in hexanes (600 mL)

الإجراء التجريبي

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),

المصدر