تفاعل #2286380

معادلة التفاعل

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

trifluoroacetic acid

→

desired product

المردود 81.0%

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

المردود 81.0%

المذيبات

DCE

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvents were removed under reduced pressure
2. 2
   workup.DISSOLUTIONthe resulting residue was re-dissolved in DCE
3. 3
   أخرىThe biphasic mixture was separated
4. 4
   استخلاصthe aqueous layer was extracted three times with DCE
5. 5
   تجفيفdried over MgSO4
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated to dryness under reduced pressure
8. 8
   أخرىThe crude product was purified by silica gel column chromatography (0 to 100% ethyl acetate/hexanes)

الإجراء التجريبي

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).

المصدر