A Concise Synthesis of a Novel Antiangiogenic Tyrosine Kinase Inhibitor

Payack, Joseph F.; Vázquez, Enrique; Matty, Louis; Kress, Michael H.; McNamara, James M.

doi:10.1021/jo048334k

Cited by 54 publications

(28 citation statements)

References 9 publications

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“…25 The cros5s-coupling of 2-indolylboronic acids suffers from protiodeborylation under conventional Suzuki cross-coupling conditions. 26 Protiodeborylation can be overcome by preparing the boronic acid or boronate in situ, but this solution limits reaction flexibility and complicates handling. 27 Nonetheless, several procedures have been reported for the crosscoupling of nitrogen heterocycles with aryl chlorides.…”

Section: Equationmentioning

confidence: 99%

Palladium-Catalyzed Cross-Coupling of Five-Membered Heterocyclic Silanolates

2008

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The preparation of π-rich 2-aryl heterocycles by palladium-catalyzed cross-coupling of sodium heteroarylsilanolates with aryl iodides, bromides and chlorides is described. The cross-coupling process was developed through extensive optimization of the follow key variables: (1) identification of stable, isolable alkali metal silanolates, (2) identification of conditions for preformation and isolation of silanolate salts, (3) judicious choice in the palladium catalyst/ligand combination, and (4) selection of the protecting group on the nitrogen of indole. It was found that the alkali metal silanolates, either isolated or formed in situ, offered a significant rate enhancement and broader substrate scope over the use of silanols activated by Brønsted bases such as NaOt-Bu. In addition, the optimized conditions for the cross-coupling of 2-indolylsilanolates were readily applied to the cross-coupling of 2-pyrrolyl-, 2-furyl-, and 2-thienylsilanolates.

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Section: Equationmentioning

confidence: 99%

Palladium-Catalyzed Cross-Coupling of Five-Membered Heterocyclic Silanolates

2008

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“…An aqueous workup, followed by crystallization from methanol, gave multi-kilogram quantities of 239. 124 Hoerrner and co-workers prepared L-756423, useful for the treatment of HIV infection, via reductive amination with STAB (Scheme 88). The reaction required 3 kg of STAB.…”

Section: Via Sodium Triacetoxyborohydridementioning

confidence: 99%

Boron Reagents in Process Chemistry: Excellent Tools for Selective Reductions

2006

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“…1-Aryl-1H-imidazoles were coupled in the 5-position with aryl bromides, iodides and triflates [389] and ethyl 4-oxazolecarboxylate was coupled in the 2-position using iodobenzene [390]. Arylation in the 2-position of an indole using 3-bromoquinolin-2(1H)-one was used in a synthesis of an antiangiogenic tyrosine kinase inhibitor [391].…”

Section: Carbon-carbon Bond-forming Reactions Using Terminal Alkynes mentioning

confidence: 99%