2-(3-CHLOROPHENYL)-1,3-THIAZOLE-4-CARBOXALDEHYDE 97 synthesis
- Product Name:2-(3-CHLOROPHENYL)-1,3-THIAZOLE-4-CARBOXALDEHYDE 97
- CAS Number:859850-99-0
- Molecular formula:C10H6ClNOS
- Molecular Weight:223.68
5198-80-1
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63503-60-6
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Yield:859850-99-0 62%
Reaction Conditions:
with tetrakis(triphenylphosphine) palladium(0);sodium carbonate in 1,2-dimethoxyethane;ethanol at 100; for 24 h;Suzuki-Miyaura Coupling;
Steps:
General procedure B for the Suzuki reaction of 2-bromothiazole-4-carboxaldehyde with arylboronic acids.
General procedure: To a microwave vial was added 2-bromothiazole-4-carboxaldehyde (0.520 mmol), Pd(PPh3)4 (60.0mg, 0.052 mmol), Na2CO3 (1.56 mmol) and the requisite aryl boronic acid (0.620 mmol). Thereaction vessel was purged with N2, before addition of degassed EtOH and 1,2-dimethoxyethane (5.0mL, (1:1)) and (2.6 mL). The reaction vessel was then sealed and heated at 100°C for 24 h. Aftercooling to room temperature the mixture was diluted with EtOAc and passed through a short pad ofCelite, eluting with EtOAc. The solution was then concentrated under reduced pressure and purifiedby column chromatography (SiO2).
References:
Bataille, Carole J.R.;Brennan, Méabh B.;Byrne, Simon;Davies, Stephen G.;Durbin, Matthew;Fedorov, Oleg;Huber, Kilian V.M.;Jones, Alan M.;Knapp, Stefan;Liu, Gu;Nadali, Anna;Quevedo, Camilo E.;Russell, Angela J.;Walker, Roderick G.;Westwood, Robert;Wynne, Graham M. [Bioorganic and Medicinal Chemistry,2017,vol. 25,# 9,p. 2657 - 2665] Location in patent:supporting information
97992-66-0
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766-84-7
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2548-79-0
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859850-99-0
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