Reacción #84131

Ecuación de reacción

benzylmethylamine

6-chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

sodium tert-butoxide

2,4 di-tert-butylphosphino-2′,4′,6′-triisopropyl biphenyl

→

benzyl-methyl-(2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-yl)-amine

Rendimiento 109.1%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGwas stirred at 100° C. for 16 h
2. 2
   FiltraciónThe reaction mixture was filtered
3. 3
   Lavadoresidue washed with EtOAc
4. 4
   ConcentraciónThe filtrate was concentrated under reduced pressure
5. 5
   Otroto afford crude material, which
6. 6
   Otrowas purified by reverse phase HPLC

Procedimiento

To a degassed mixture of 6-chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (100 mg, 0.5 mmol), sodium tert-butoxide (576 mg, 6.0 mmol), palladium acetate (22.4 mg, 0.1 mmol) and 2,4 di-tert-butylphosphino-2′,4′,6′-triisopropyl biphenyl (63.0 mg, 0.15 mmol) was added dry toluene (2 mL). After stirring for 5 min, benzylmethylamine (0.09 mL, 0.7 mmol) was added to the reaction mixture, which was stirred at 100° C. for 16 h. The reaction mixture was filtered and residue washed with EtOAc. The filtrate was concentrated under reduced pressure to afford crude material, which was purified by reverse phase HPLC to yield benzyl-methyl-(2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-yl)-amine (50 mg). 1H NMR (Freebase, CDCl3) δ (ppm): 7.80 (bs, 1H), 7.38 (m, 4H), 7.28 (m, 1H), 7.10 (s, 1H), 7.0 (t, 1H), 6.78 (d, 1H), 4.28 (s, 2H), 3.70 (s, 2H), 2.86 (m, 4H), 2.78 (s, 3H), 2.58 (s, 3H).

Fuente