LH-Indole, 3-

NOl H°- N2H4 H20/Raney-Ni/C2Hs — OH 20-25° 1 h Hj/Pd — C/CZH sOH Normaldruck 20-25° 5 h 4-Amino-l-(2,3-dideoxy-j3-d-glycero-pen t-2-enofurano-syl)-lH-indol 4-Amino-1-( 2,3-dideoxy-fl-D-glycero-pen tofuranosyl) -lH-indol 85 70 1 1... 

Chemical Name 2-Propanol, l-((l,l-dimethylethyl)amino)-3-((2-methyl-lH-indol-4-yl)oxy)-, benzoate (ester), (+/-)-... 

SYNS CY-39 3-(2-(DIMETHYLAMINO)ETHYL)-lH-INDOL-4-OL DIHYDROGEN PHOSPHATE ESTER 3-2 -DIMETHYLAiMINOETHYLINDOL-4-PHOSPHATE 3-(2-DIMETHYLAMINOETHYL)INDOL-4-YL DIHYDROGEN PHOSPHATE INDOCYBIN PSILOCIN PHOSPHATE ESTER PSILOCIPIN PSILOTSIBIN TEON-ANACATL... 

DIMETHYLAMINO)ETHYL)-lH-INDOL-4-OL DIHYDROGEN PHOSPHATE ESTER see PHU500... 

The tricyclic system has also been constructed from an indole via electrophilic substitution reactions at positions 3 and/or 4. Synthesis of tricyclic ergoline synthons from 5-methoxy-lH-indole-4-carboxaldehyde has been described [45]. Sodium cyanoborohydride mediated reductive amination provided easy access to l,3,4,5-tetrahydrobenz[cd]indole-4-amines, compounds which show specificity for serotonin and dopamine receptors. 

Suginome and coworkers discovered the novel [3+2] regioselective photoaddilion of 2-amino-1,4-naphthoquinones with electron-rich alkenes to afford lH-benz[/] indole-4,9-diones (Schane 16, equation 1) [112]. Likewise, amino-1,4-benzoquinones with alkenes gave lH-indole-4,7-diones (equation 2). If the initial photoproducts could not indolize by loss of alcohoL then the corresponding dihydro compounds were isolated. Parker and Mindt found that qui-none monoimides were smoothly photocyclized to the respective 5-hydroxyindoles (equation 3) [113]. 

Dimethylaminoethyl)-lH-indol-4-yl dihydrogen phosphate (jjsilocybin), the O-phosphoryl-4-hydroxy... 

UV, 4, 179 <71PMH(3)94> lH-Indole-6-carboxylic acid UV, 4, 179 <71PMH(3)94) lH-Indole-7-carboxylic acid... 

One year later Van der Eycken and Dehaen described the smooth microwave-assisted borylation of 4, 5, 6 and 7-bromo-lff-indole using PdCl2(dppf) as a precatalyst and KOAc as a base (Scheme 30) [48]. With 5, 6, and 7-bromo-lH-indole, DMSO was used as solvent at a temperature of 150 °C (with a set power of 150 W) for 17-27 min, resulting in the corresponding boronate esters in good yields. For 4-bromo-lH-indole, DME gave a better result at the same temperature (with a set power of 250 W). 

Remarkably, one year later Leadbeater described that biaryls can be synthesized via a Suzuki-type coupling under transition-metal free conditions [51, 52]. The reaction conditions were almost identical to those reported for the ligand-free process, with the difference being that a larger amoimt of Na2C03 and arylboronic acid were used. Only one successful example of a heteroaryl haUde substrate is shown namely, the coupling of 2-bromopyridine with phenylboronic acid (Scheme 32). 3-Bromothiophene did not couple under the same reaction conditions. Unfortimately, attempts to use heteroarylboronic acids such as 3-pyridinylboronic acid, 3-thienylboronic acid, and lH-indol-5-ylboronic acid on 4-bromoacetophenone completely failed. 

CN ( )-l-(4-chlorobenzoyl)-5-methoxy-2-methyl-lH-indole-3-acetic acid 2-I4-[3-[[4-(benzoylamino)-5-(dipropylamino)-1,5-dioxopentyl]oxy]propyl]-1 -piperazinyl]ethyl ester... 

CN [3-[[2-methoxy-4-[[[(2-methylphenyl)sulfonyl]amino]carbonyl]phenyl]methyl]-l-methyl-lH-indol-5-yl]carbamic acid cyclopentyl ester... 

CgH N, 26955-79-i) see Sulfaphenazole ( )-3-phenyl-3-hydroxy-l-propanamine (CjHijNO 5053-63-4) see Fluoxetine iV-(3-phenyl-lH-indol-l-yl)acetamide (C1SH14N2O 57647-16-2) see Binedaline phenyl isocyanate... 

Recently, SB-269970 (l-[3-hydroxy-phenyl-sulphonyl]-2-[2-(4-methyl-l-piperidinyl)-ethyl] pyrrolidine) and SB-656104 (6-((R)-2- 2-[4-(4-chloro-phenoxy)-piperidin-l-yl]-ethyl pyrrolidine-l-sulphonyl)-lH-indole) have been reported to be potent 5-HT7 receptor antagonists (Hagan et al., 2000 Forbes et al., 2002). Selective 5-HT7 receptor agonists are not available at the present time. Systemic administration of SB-269970 or SB-656104 to rats at the beginning of the light period has been shown to reduce the total amount of REMS and to increase REMS latency. Values of W and SWS were not significantly modified (Hagan et al., 2000 Thomas et al., 2003). Hedlund et al. (2005) established that 5-HT7... 

In 2001, Knaack and co-workers56 reported an application of the INADEQUATE experiment in the course of synthesizing and characterizing a biologically active 2-[l-(4-chlorobenzyl)-lH-indol-3-yl]-2-oxo-N-pyri-din-4-yl acetamide (6). Treatment of l-(4-chlorobenzyl)-lH-indole with oxalyl chloride afforded the corresponding oxoacetyl chloride that was finally subjected to aminolysis with 4-aminopyridine to afford the final product of the reaction scheme, 6. Although the NMR data supported the N-benzyl structure, a 1,1-ADEQUATE spectrum was acquired to provide additional confirmation of the structure of 6. 

Greenbeger LM, Annable T, Collins KI, Komm BS, Lyttle CR, Miller CP, et al. (2001) A new antiestrogen, 2-(4-hydroxy-phenyl)-3-methyl-l-[4-(2-piperidin-l-yl-ethoxy)-benzyl]-lH-indol-5-ol hydroclorhide (ERA-923), inhibits the growth of tamoxifen-sensitive and -resistant tumors and is devoid of uterotropic effects in mice and rats. Clin Cancer Res 7 3166-3177... 

The solid state photochemical reaction of indole with 1,4-naphthoquinone yielded 5H-dinaphtho(2,3-a 2, 3 -c)carbazole-6,ll,12,17-tetrone in addition to 2-(3-indolyl)-1,4-naphthoquinone which was also the only product in the solution photoreaction. Solventless thermochemical reactions of indole with phenanthrenequinone in the presence or absence of zinc chloride gave 10-(lH-indol-3-yl)-9-phenanthrenol and 9,10-dihydro-9-(lH-indol-3-yl)-10-(3H-indol-3-ylidene)-9-phenanthrenol or 10,10-di-lH-indol-3-yl-9(10H)-phenanthrenone, respectively. All of these products were only obtained in trace amounts in corresponding solution reactions, and are different from the adduct 10-hydroxy-10-(lH-indol-3-yl)-9(10H)-phenanthrenone obtained in the solution photoreaction (Wang et al., 1998). 

Synthesis of high Tg co-polycarbonates containing 3,3-bis(4-hydroxyphenyl)-l-phenyl-lH- indol-2-one and bisphenol A biphenols, which adhere to aluminum. 

TABLE 1. Physical Properties of Polycarbonate Prepared Using Bisphenol A, 3,3-bis(4-hydroxy-phenyl)-l-phenyl-lH-indol-2-one, and Phosgene Dissolved in C Cb/Chlorobenzene at Ambient Temperature... 

Dimethyl-4-oxo-2,3,4,5,6,7-hexahydro-lH-indole-6-carb xyKc add]-L-Lactyl-Glu-Ala-Leu-Ala-Lys-Ala-NH2 General Procedure for the Attachment of a Peptide to 2-( f6-(tert-Butoxycarbonyl)-3,6-dimethyl-4-oxo-2,3,4,5,6,7-hexahydro-lH-indol-3-yl]carbonyl oxy)propanoic Acid 1 201... 

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