An Efficient Synthesis of 5‐Bromopyridine‐2‐carbonitrile.

Markevitch, David Y.; Rapta, Miroslav; Hecker, Scott J.; Renau, Thomas E.

doi:10.1002/chin.200350143

Cited by 3 publications

(4 citation statements)

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“…64 The preparation of dipyridylbenzene derivatives 23−29 is shown in Scheme 3. 3-Bromopyridyl starting materials 57 (also commercially available) and 58 were prepared by treatment of 5-bromo-N-(tert-butyl)picolinamide 73 or 5-bromonicotinamide with phosphorus oxychloride. 73 The reactions of compounds 57 and 58 with bis(pinacolato)diboron and catalytic PdCl 2 (dppf) 74 gave boronate esters 59 and 60, which underwent Suzuki coupling with 1,3-diiodobenzene under anhydrous conditions (Pd(PPh 3 ) 4 , Ag 2 CO 3 , THF) 75 to give 1,3-di(pyridin-3-yl)benzenedinitriles 61 and 62 (60% and 69% yields).…”

Section: ■ Chemistrymentioning

confidence: 99%

“…Combined dried extracts were evaporated to a white solid (2.16 g, 87%), which was recrystallized from EtOH to give a white solid (1.24 g, 50%): mp 153−154 °C; 1 H NMR δ 7.65 (t, J = 1.6 Hz, 1H), 7.53 (d, J = 1.6 Hz, 2H), 7.13 (t, J = 7.8 Hz, 2H), 6.92 (t, J = 1.9 Hz, 2H), 6.86 (dd, J = 7.6 and 0.9 Hz, 2H), 6.62 (ddd, J = 8.0, 2.2, and 0.9 Hz, 2H), 5. 3-Bromo-4′-nitrobiphenyl (73). 73 was prepared from iodobenzene 51 (5.76 g, 20.4 mmol) and 4-nitrophenylboronic acid pinacol ester (5.04 g, 20.2 mmol).…”

Section: Journal Of Medicinal Chemistrymentioning

confidence: 99%

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Synthesis and Antiprotozoal Activity of Dicationic m-Terphenyl and 1,3-Dipyridylbenzene Derivatives

et al. 2013

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4,4″-Diamidino-m-terphenyl (1) and 36 analogues were prepared and assayed in vitro against T rypanosoma brucei rhodesiense , Trypanosoma cruzi , Plasmodium falciparum , and Leishmania amazonensis . Twenty-three compounds were highly active against T. b. rhodesiense or P. falciparum. Most noteworthy were amidines 1, 10, and 11 with IC50 of 4 nM against T. b. rhodesiense, and dimethyltetrahydropyrimidinyl analogues 4 and 9 with IC50 values of ≤ 3 nM against P. falciparum. Bis-pyridylimidamide derivative 31 was 25 times more potent than benznidazole against T. cruzi and slightly more potent than amphotericin B against L. amazonensis. Terphenyldiamidine 1 and dipyridylbenzene analogues 23 and 25 each cured 4/4 mice infected with T. b. rhodesiense STIB900 with four daily 5 mg/kg intraperitoneal doses, as well as with single doses of ≤ 10 mg/kg. Derivatives 5 and 28 (prodrugs of 1 and 25) each cured 3/4 mice with four daily 25 mg/kg oral doses.

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Section: ■ Chemistrymentioning

confidence: 99%

Section: Journal Of Medicinal Chemistrymentioning

confidence: 99%

Synthesis and Antiprotozoal Activity of Dicationic m-Terphenyl and 1,3-Dipyridylbenzene Derivatives

et al. 2013

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“…While 2,4-dicyanopyridine is commercially available through convenient and affordable sources, and 5-bromo-2cyanopyridine can be prepared following literature procedure, 24 2,5-dicyanopyridine was not easily purchased at an affordable price nor were the published preparations 25 convenient. Thus, the synthesis of 2,5-dicyanopyridine via a previously unreported route, but employing well-established organic synthetic transformations, was deemed the best option.…”

Section: Synthesismentioning

confidence: 99%

Manipulating the crystal packing of pyDTDA radical ligand coordination complexes with Mn(ii) and Ni(ii)

et al. 2009

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The synthesis of 4'-CN, 5'-CN and 5'-Br substituted pyDTDA neutral radical bidentate ligands is reported (pyDTDA = 4-(2'-pyridyl)-1,2,3,5-dithiadiazolyl). The Ni(hfac)(2) and Mn(hfac)(2) coordination complexes of both cyano substituted ligands, and the Mn(hfac)(2) coordination complex of the bromo substituted ligand, have been prepared and the crystal packing of these is compared (hfac = 1,1,1,5,5,5-hexafluoroacetylacetonato-). Unlike the previously reported Mn(hfac)(2)(pyDTDA), the Mn(hfac)(2)(4'-CN-pyDTDA) complex does not form dimers in the solid-state making it possible to measure the magnetic coupling between the unpaired electrons on the coordinated Mn(ii) ion and the unpaired electron on the radical ligand by SQUID magnetometry; J/k(B) = -74(1) K, using H = -2J{S(Mn).S(Rad)} and g(av.) = 2.01.

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“…was prepared according to general method B starting from 3-ethynyl-4-methyl-N-(3-(trifluoromethyl)phenyl)benzamide (0.16 g, 0.54 mmol) and 5-bromo-N-methylpicolinamide 29 (0.089 g, 0.41 mmol) to give 13c as a white solid (0.086 g, 48%): 1 H NMR (400 MHz, acetone-d 6 ) δ ppm 9.89 (s, 1 H), 8.79 (s, 1 H), 8.38 (s, 1 H), 8.33 (s, 1 H), 8.21 (d, J ) 1.5 Hz, 1 H), 8.17 (s, 2 H), 8.12 (d, J ) 8.1 Hz, 1 H), 8.01 (dd, J ) 7.9, 1.6 Hz, 1 H), 7.61 (t, J ) 7.9 Hz, 1 H), 7.52 (d, J ) 8.1 Hz, 1 H), 7.47 (d, J ) 7.7 Hz, 1 H), 2.98 (d, J ) 4.8 Hz, 3 H), 2.61 (s, 3 H); HRMS m/z ) 460.1247…”

Section: N-methyl-5-(2-(2-methyl-5-((3-(trifluoromethyl)phenyl)carbam...mentioning

confidence: 99%

Alkynylpyrimidine Amide Derivatives as Potent, Selective, and Orally Active Inhibitors of Tie-2 Kinase

et al. 2007

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The recognition that aberrant angiogenesis contributes to the pathology of inflammatory diseases, cancer, and myocardial ischemia has generated considerable interest in the molecular mechanisms that regulate blood vessel growth. The receptor tyrosine kinase Tie-2 is expressed primarily by vascular endothelial cells and is critical for embryonic vasculogenesis. Interference with the Tie-2 pathway by diverse blocking agents such as soluble Tie-2 receptors, anti-Tie-2 intrabodies, anti-Ang-2 antibodies, and peptide-Fc conjugates has been shown to suppress tumor growth in xenograft studies. An alternative strategy for interfering with the Tie-2 signaling pathway involves direct inhibition of the kinase functions of the Tie-2 receptor. Herein we describe the development of alkynylpyrimidine amide derivatives as potent, selective, and orally available ATP-competitive inhibitors of Tie-2 autophosphorylation.

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An Efficient Synthesis of 5‐Bromopyridine‐2‐carbonitrile.

Cited by 3 publications

References 1 publication

Synthesis and Antiprotozoal Activity of Dicationic m-Terphenyl and 1,3-Dipyridylbenzene Derivatives

Synthesis and Antiprotozoal Activity of Dicationic m-Terphenyl and 1,3-Dipyridylbenzene Derivatives

Manipulating the crystal packing of pyDTDA radical ligand coordination complexes with Mn(ii) and Ni(ii)

Alkynylpyrimidine Amide Derivatives as Potent, Selective, and Orally Active Inhibitors of Tie-2 Kinase

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