Sodium Azide → 2-Pyridinemethanamine, 5-(2,2,2-trifluoroethoxy)-

温度

0 °C

Dissolve sodium azide (270 mg, 4.0 mmol) in DM (30 mL). Cool the solution to 0° C., then add 2-bromomethyl-5-(2,2,2-trifluoroethoxy)-pyridine (440 mg, 1.6 mmol) at 0° C. Slowly heat the mixture from 0° C. to 80° C. over 30 min. Cool the reaction, dilute with EtOAc (100 mL) and wash with 10% aqueous NaCl (3×25 mL). Collect the organic layer and concentrate in vacuo to a volume of 50 mL. Transfer the solution to a pressure vessel. Add 10% Pd/C (Degussa type E101, 50% water by wt, 500 mg) and pressurize the vessel under hydrogen (10 psi) for 1 h with stirring. Filter the mixture through Celite® and wash filter cake with warm methanol followed by DCM. Concentrate in vacuo, then purify by chromatography on silica gel eluting with DCM/2M ammonia in methanol (20:1) to obtain the title compound (180 mg, 54%). MS (ES+) m/z: 207 (M+H)+.

1. customat 0° C
2. temperatureSlowly heat the mixture from 0° C. to 80° C. over 30 min
3. temperatureCool
4. customthe reaction
5. washwash with 10% aqueous NaCl (3×25 mL)
6. customCollect the organic layer
7. concentrationconcentrate in vacuo to a volume of 50 mL
8. additionAdd 10% Pd/C (Degussa type E101, 50% water by wt, 500 mg)
9. customfor 1 h
10. filtrationFilter the mixture through Celite®
11. washwash
12. filtrationfilter cake with warm methanol
13. concentrationConcentrate in vacuo
14. custompurify by chromatography on silica gel eluting with DCM/2M ammonia in methanol (20:1)

ORDレコード

ord-8c7ec263325740aa99b5dd2952665214

出典データセット

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08022062B2