反応 #2328997

反応方程式

NaOH

trifluoroacetic acid

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

Water

→

title compound

収率 41.8%

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

収率 41.8%

溶媒

CH2Cl2

CH2Cl2

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他the layers separated
3. 3
   抽出The aqueous layer was extracted with CH2Cl2 (3×)
4. 4
   乾燥The combined organic layers were dried (Na2SO4)
5. 5
   ろ過filtered
6. 6
   濃縮concentrated
7. 7
   その他Purification

実験手順

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).

出典