Reacción #218142

Ecuación de reacción

6-(2,3-difluoro-4-formyl-phenoxy)-nicotinamide

n-pentylamine

NaBH4

→

title compound

Rendimiento 83.0%

6-(2,3-Difluoro-4-pentylaminomethyl-phenoxy)-nicotinamide

Rendimiento 83.0%

Disolventes

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónbefore concentrating
2. 2
   workup.DISSOLUTIONDissolve
3. 3
   Concentraciónconcentrate in EtOAc
4. 4
   Lavadowash with 5% aq. KOH and brine
5. 5
   Secadodry (Na2SO4)
6. 6
   Concentraciónconcentrate
7. 7
   OtroPurify on silica gel (5% (1 M NH3/MeOH)/DCM)

Procedimiento

Combine 6-(2,3-difluoro-4-formyl-phenoxy)-nicotinamide (278 mg, 1.00 mmol), n-pentylamine (105 mg, 1.20 mmol), and MeOH (3 ml) in a round bottom flask equipped with nitrogen inlet and stir for two hours. Add NaBH4 (57 mg, 1.50 mmol) and stir for an additional two hours before concentrating. Dissolve concentrate in EtOAc and wash with 5% aq. KOH and brine, dry (Na2SO4), and concentrate. Purify on silica gel (5% (1 M NH3/MeOH)/DCM) to give the title compound (290 mg) as a white solid. Mass spectrum (ion spray): m/z=350 (M+1); 1H NMR (DMSO-d6): 8.55 (s, 1H), 8.28 (d, 1H), 8.03 (s, 1H), 7.50 (s, 1H), 7.29 (m, 1H), 7.22 (d, 1H), 7.15 (m, 1H), 3.73 (s, 2H), 2.48 (t, 2H), 1.41 (m, 2H), 1.25 (m, 4H), 0.84 (m, 3H).

Fuente