Reacción #454010

Ecuación de reacción

13

3-(tert-butyloxycarbonyl)-1-chloromethyl-5-nitro-1,2-dihydro-3H-benz[e]indole

EDCI.HCl

(E)-3-methoxycinnamic acid

→

14l

Rendimiento 74.0%

1-(chloromethyl)-3-[(E)-3-methoxycinnamoyl]-5-nitro-1,2-dihydro-3H-benz[e]indole

Rendimiento 74.0%

Disolventes

DMA

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrogave a solid
2. 2
   OtroThis was recrystallised from CH2Cl2 /i-Pr2O

Procedimiento

Deprotection of 13 (250 mg, 0.69 mmol) as in Example C above, and reaction of the product with EDCI.HCl (331 mg, 1.73 mmol), (E)-3-methoxycinnamic acid (129 mg, 0.72 mmol) and DMA (3 mL) at 20° C. for 3 h, followed by addition of dilute KHCO3, gave a solid. This was recrystallised from CH2Cl2 /i-Pr2O followed by EtOAc to give 14l (215 mg, 74%), mp 200° C. 1H NMR [(CD3)2SO] δ 9.22 (s, 1 H, H-4), 8.33 (dd, J=7.9, 1.8 Hz, 1 H, H-6), 8.19 (dd, J=7.5, 1.7 Hz, 1 H, H-9), 7.78-7.68 (m, 2 H, H-7,8), 7.72 (d, J=15.4 Hz, 1 H, PhCH=CH), 7.45-7.34 (m, 2 H, H-5',6'), 7.39 (s, 1 H, H-2'), 7.26 (d, J=15.4 Hz, 1 H, PhCH=CH), 7.02 (dt, J=7.2, 2.2 Hz), 1 H, H-4'), 4.71-4.56 (m, 3 H, H-1,2), 4.11-4.05 (m, 2 H, CH2Cl), 3.84 (s, 3 H, CH3). Anal. Calculated for C23H19ClN2O4 : C, 65.3; H, 4.5; N, 6.6; Cl, 8.4. Found: C, 65.0; H, 4.6; N, 6.6; Cl, 8.5%.

Fuente