تفاعل #2286395

معادلة التفاعل

di(tert-butyl) 4-fluoro-2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-ylimidodicarbonate

trifluoroacetic acid

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product

المردود 68.8%

[4-fluoro-2-(5-fluoro-pyridin-3-yl)-thiazol-5-yl]-carbamic acid tert-butyl ester

المردود 68.8%

المذيبات

DCM

ظروف التفاعل

المعالجة

1. 1
   أخرىbefore quenched slowly with saturated NaHCO3 solution
2. 2
   أخرىThe organic layer was separated
3. 3
   استخلاصthe aqueous layer was extracted with dichloromethane (DCM)
4. 4
   تجفيفThe combined organic layer was dried over Na2SO4
5. 5
   ترشيحfiltered
6. 6
   أخرىpurified by silica gel chromatography (0 to 100% ethyl acetate/hexanes)

الإجراء التجريبي

To a solution of di(tert-butyl) 4-fluoro-2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-ylimidodicarbonate (320 mg, 0.77 mmol) in DCM (7 mL) was added trifluoroacetic acid (TFA) (0.7 mL). The solution was stirred at room temperature for 10 minutes, before quenched slowly with saturated NaHCO3 solution. The organic layer was separated and the aqueous layer was extracted with dichloromethane (DCM). The combined organic layer was dried over Na2SO4, filtered and purified by silica gel chromatography (0 to 100% ethyl acetate/hexanes) to give product as a pale yellow solid (166 mg, 68%): mp 188-191° C.; 1H NMR (300 MHz, CDCl3) δ 8.84 (s, 1H), 8.46 (d, J=2.7 Hz, 1H), 7.85 (ddd, J=9.1, 2.6, 1.7 Hz, 1H), 6.92 (br s, 1H), 1.55 (s, 9H); ESIMS m/z 312 (M−1).

المصدر