Réaction #2328997

Équation de réaction

NaOH

trifluoroacetic acid

tert-Butyl (2-fluoroethyl)[5-(6-methoxy-1,3-benzoxazol-2-yl)pyridin-2-yl]carbamate

Water

→

title compound

Rendement 41.8%

N-(2-fluoroethyl)-5-(6-methoxy-1,3-benzoxazol-2-yl)pyridin-2-amine

Rendement 41.8%

Solvants

CH2Cl2

CH2Cl2

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   Autrethe layers separated
3. 3
   ExtractionThe aqueous layer was extracted with CH2Cl2 (3×)
4. 4
   SéchageThe combined organic layers were dried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   AutrePurification

Mode opératoire

tert-Butyl (2-fluoroethyl)[5-(6-methoxy-1,3-benzoxazol-2-yl)pyridin-2-yl]carbamate (0.65 mmol) was dissolved in CH2Cl2 (20 mL), trifluoroacetic acid (0.5 mL) was added and the reaction mixture was stirred for 4 hours at r.t. Water (20 mL), NaOH (1.5 mL, 5M aq., pH adjusted to 12) and CH2Cl2 (20 mL) was added and the layers separated. The aqueous layer was extracted with CH2Cl2 (3×). The combined organic layers were dried (Na2SO4) filtered and concentrated. Purification using reverse phase HPLC afforded the title compound (78.0 mg). 1H NMR δ ppm 8.74 (d, 1H) 8.03 (dd, 1H) 7.60-7.64 (m, 1H) 7.58 (d, 1H) 7.35 (d, 1H) 6.95 (dd, 1H) 6.70 (d, 1H) 4.60-4.66 (m, 1H) 4.47-4.54 (m, 1H) 3.82 (s, 3H) 3.67-3.74 (m, 1H) 3.60-3.67 (m, 1H); ESI-MS m/z 288 (M+H).

Source