4- fluorophenyl 4-methoxyphenyl

Chemical Name 1-[(4-Fluorophenyl)methyl] -N-[1 -[2-(4-methoxyphenyl)ethyl] -4-piperi-dinyl] -1 H-benzimidazol-2-amine... 

Martin effected the synthesis of several 3,5-diarylated indoles by a tandem Stille-Suzuki sequence [131]. The latter reaction involves exposure of 3-(3-pyridyl)-5-bromo-l-(4-toluenesulfonyl)indole with arylboronic acids (aryl = 3-thienyl, 2-furyl, phenyl) under typical conditions to give the expected products in 86-98% yield [131], Carrera engaged 6- and 7-bromoindole in Pd-catalyzed couplings with 4-fluoro- and 4-methoxyphenylboronic acids to prepare 6- and 7-(4-fluorophenyl)indole (90% and 74% yield) and 6-(4-methoxyphenyl)indole (73% yield) [29]. Banwell and co-workers employed 7-bromoindole in a Suzuki coupling with 3,4-dioxygenated phenylboronic acids en route to the synthesis of Amaryllidaceae alkaloids [132], Yields of 7-arylated indoles are 93-99%. Moody successfully coupled 4-bromoindole... 

D(p-F)PPAP (lOe) 6-bis(4-fluorophenyl)-phosphino-2-(pivaloylamino)pyridine, 3-D(p-MeO) PICon (11b) 3-bis(4-methoxyphenyl)phosphinoisoquinolone, 3-D(p-F)PICon (lid) 3-bis(4-fluorophenyi)phosphinoisoquinolone. 

A mixture of 2.3 parts of 2-(4-methoxyphenyl)ethyl methanesulfonate, 4.9 parts of l-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-lH-benzimidazol-2-amine dihydrobromide, 3.2 parts of sodium carbonate, 0.1 part of potassium iodide and 90 parts of N,N-dimethylformamide is stirred overnight at 70°C. The reaction mixture is poured onto water. The product is extracted with methylbenzene. The extract is washed with water, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (98 2 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 2,2 -oxybispropane, yielding 2.2 parts (48%) of 1-(4-fluorophenylmethyl)-N-[l-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]-lH-benzimidazol-2-amine MP 149.1°C. 

Chemical Name 1-Butanone, l-(4-fluorophenyl)-4-(4-(2-methoxyphenyl)-l-piperazinyl)-... 

To 20% solution of phosgene in toluene, agitated and cooled to 0°C, are added over 30 min a solution of l-p-fluoro-benzoyl-l-hydroxy-3-N-[N -(2-methoxyphenyl)]piperazinopropane and triethylamine in anhydrous chloroform. It is agitated at ambient temperature for 5 h, cooled to 0°C and the solution saturated with gaseous ammonia. The solution is agitated at ambient temperature for 3 h, filtered and the filtrate dried under reduced pressure, 4-p-fluorophenyl-5-p-(4-o-methoxyphenylpiperazino)ethyl-4-oxazolin-2-one, melting point 154°C (by alcohol) was obtained. 

The patent describes only synthetic pathways and chemical experimental data of prepared compounds (14). No biological data were reported. Deljac et al. (1992) described compounds of symmetric bisquatemary imida-zolium type with a four-carbon linker (Figure 66.12), where R is methyl (15a, 16a), phenyl (15b, 16b), benzyl (15c, 16c), 4-methoxyphenyl (15d, 16d), and 4-fluorophenyl (15e, 16e). 

Substituents in the aryl ring, too, can exert their own directional effects a p-nitro group deactivates the benzene ring and directs further attack into the heterocyclic ring in 4-(3, 4-dichlorophenyl)imidazole nitration is mainly at C-5 in 4-(p-methoxyphenyl)imidazole (195) subsequent nitration takes place adjacent to the methoxy function and then at C-5 (Scheme 104) (77CHE1110). The nitration of 2-(p-fluorophenyl)imidazole has been discussed earlier (Section 4.07.1.4.2). 

The 3-methoxyphenyl- (12a) (IC50 < 3.2 pM) and the 3-fluorophenyl-(12b) derivatives showed even higher cytotoxic activity than the unsubstituted compound (12). An insignificant electronic effect of the substituents in the aromatic ring is observed. The respective aroylindoles... 

---