8
P. UMAREDDY AND V. R. ARAVA
Developed plates were visualized by using UV light or in an iodine chamber. HPLC was
performed by using a Shimadzu 2010 instrument. The HRMS data of new compounds
General procedure for syntheses of 4
To a stirred solution of FeCl3 (5.0 g, 0.030 mol) and DCM (50 mL) was added a solution
of 3 (5.0 g, 0.020 mol in 15 mL of DCM) at 5–10 ꢀC for 15 min. The mixture was stirred
at room temperature. After completion of the reaction (monitored by TLC) the reaction
mass was quenched into water and stirred for 30 min. The organic layer was separated
and the aqueous layer was extracted with DCM. The combined organic layer was
washed with 5% hydrazine hydrate solution and the solvent was evaporated to get 4
which were purified on silica gel column and the pure compound was isolated as
a solid.
6,6’-Dimethoxy-3,3’-diphenyl-[2,2’]bibenzofuranyl (4a)
MP: 162.4–164.8 ꢀC; yield 68%; IR (KBr in, cmꢁ1): 2829, 1621, 1489, 1272, 1105, 813,
695, 564; 1 H NMR (400 MHz, CDCl3) (d ppm): 7.50 (d, J ¼ 8.5 Hz, 1H), 7.33–7.32
(m, 2H), 7.26–7.25 (m, 3H), 7.05 (s, 1H), 6.93 (d, J ¼ 8.48 Hz, 1H), 3.88 (s, 3H, OCH3),
13C NMR (100 MHz, CDCl3) (d ppm): 158.97, 155.98, 141.61, 131.81, 129.16, 128.32,
127.30, 121.90, 121.48, 120.75, 112.52, 95.86, 55.80; HRMS (ESI): [M þ H]þ calcd. for
C30H22O4, 446.1518; found, 446.1517.
General procedure for syntheses of 8
To a stirred solution of 7 (10.0 g, 0.044 mol) and methanol (20 ml) and ethyl acetate
(20 ml) added molecular I2 (6.8 g, 0.026 mol), respectively at room temperature. The
mixture was maintained at room temperature. After completion of the reaction (moni-
tored by TLC) reaction mass was concentrated under vacuum and saturated Na2S2O3
(20 ml) were added, and the mixture was extracted with ethyl acetate (2 ꢂ 100 mL).
The combined organic layers were washed with brine and concentrated in vacuum.
The crude product was crystallized from methanol to afford the desired bis indole
product 8.
6,6’-Dimethoxy-2,2’-biphenyl-1H,1’H-[3,3’] biindolyl (8a)
MP: 158–161.5 ꢀC; Yield: 90%; IR (KBr in, cmꢁ1): 3399, 2937, 1717, 1624, 1447, 1254,
1
767; H NMR (400 MHz, DMSO) (d ppm): 8.23 (S, 1H, NH), 7.28 (d, J ¼ 7.2 Hz, 2H),
7.25–7.06 (m, 4H), 6.94 (s, 1H), 6.67–6.50 (dd, J1¼2.4 Hz, J2¼2.0 Hz, 1H), 3.80 (s, 3 H,
OCH3); 13C NMR (100 MHz, DMSO) (d ppm): 156.76, 137.09, 133.89, 133.23, 128.40,
126.66, 126.47, 124.43, 121.30, 109.66, 107.32, 94.56, 55.70; HRMS (ESI): [M þ H]þ
calcd. for C30H22N2O2, 444.1838; found, 444.1839.