Reaction #465979

Reaction equation

NaBH4

methyl 4-chloro-6-trifluoromethylpyridine-2-carboxylate

NaN3

H2O

H2O

→

Methyl 4-Amino-6-trifluoromethylpyridine-2-carboxylate

Solvents

DMF

MeOH

Conditions

Workup

1. 1
   Extractionextracted (3×) with Et2O
2. 2
   ConcentrationThe organic layer was concentrated
3. 3
   Otherto yield a white solid
4. 4
   Extractionextracted (3×) with Et2O
5. 5
   DryingThe extract was dried over MgSO4
6. 6
   Concentrationconcentrated
7. 7
   OtherThe resulting residue was purified via flash column chromatography
8. 8
   Otherto give 0.95 of product as a white solid

Procedure

To a solution of methyl 4-chloro-6-trifluoromethylpyridine-2-carboxylate (2.44 g, 10.2 mmol) in aqueous DMF was added NaN3 (0.7 g, 10.8 mmol). The resulting mixture was heated at 70° C. for 18 hr, added to H2O and extracted (3×) with Et2O. The organic layer was concentrated to yield a white solid that was dissolved in 10 mL of MeOH. Excess NaBH4 was added and the reaction mixture stirred at RT for 0.5 hr. This material was added to H2O, extracted (3×) with Et2O. The extract was dried over MgSO4 and concentrated. The resulting residue was purified via flash column chromatography to give 0.95 of product as a white solid; mp 114° C.

Source