{"id":5110,"date":"2021-07-02T03:51:13","date_gmt":"2021-07-01T19:51:13","guid":{"rendered":"https:\/\/www.pyrazoles-derivatives.com\/?p=5110"},"modified":"2021-07-02T03:51:13","modified_gmt":"2021-07-01T19:51:13","slug":"introduction-of-a-new-synthetic-route-about-c7h10n2o","status":"publish","type":"post","link":"https:\/\/www.pyrazoles-derivatives.com\/?p=5110","title":{"rendered":"Introduction of a new synthetic route about C7H10N2O"},"content":{"rendered":"

These common heterocyclic compound, 2644-93-1, name is 1,3,5-Trimethyl-1H-pyrazole-4-carbaldehyde, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: pyrazoles-derivatives<\/a><\/p>\n

To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (1.37 g, 3.86 mmol, Intermediate 10: step d) was added THF (45 mL) at room temperature which resulted in a colorless homogeneous mixture. The solution was cooled to -78 C. and then n-BuLi (2.5 M in hexanes, 1.8 mL, 4.5 mmol) was added dropwise. The color of the solution became a reddish-brown color. After 4 minutes, 1,3,5-trimethyl-1H-pyrazole-4-carbaldehyde (300 mg, 2.17 mmol, in 3 mL THF) was introduced and the color of the mixture changed from reddish-brown to a yellow-greenish color over 5 minutes. The mixture was allowed to warm to 0 C. over 45 minutes at which time the reaction was quenched with aqueous NH4Cl solution. The mixture was diluted further with water and extracted with EtOAc (3*150 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to give a light orange foam. FCC on silica gel (2% MeOH-DCM increasing to 8% MeOH-DCM) afforded the title compound as a light yellow amorphous solid. 1H NMR (500 MHz, CDCl3) delta ppm 8.23 (s, 1H), 7.78 (d, J=8.6 Hz, 1H), 7.56-7.47 (m, 3H), 7.40 (d, J=8.1 Hz, 2H), 6.01 (d, J=3.0 Hz, 1H), 4.35 (s, 2H), 4.06 (s, 3H), 3.70 (s, 3H), 2.14 (s, 3H), 2.12 (s, 3H), 2.09 (d, J=3.3 Hz, 1H). MS (ESI): mass calcd. for C25H23ClF3N3O2, 489.1; m\/z found, 490.1 [M+H]+.<\/p>\n

The synthetic route of 1,3,5-Trimethyl-1H-pyrazole-4-carbaldehyde has been constantly updated, and we look forward to future research findings.<\/p>\n

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; US2015\/105372; (2015); A1;<\/a>,
Pyrazole – Wikipedia<\/a>,
Pyrazoles – an overview | ScienceDirect Topics<\/p>\n","protected":false},"excerpt":{"rendered":"

The synthetic route of 1,3,5-Trimethyl-1H-pyrazole-4-carbaldehyde has been constantly updated, and we look forward to future research findings.<\/p>\n","protected":false},"author":8,"featured_media":0,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[391,131],"tags":[126],"class_list":["post-5110","post","type-post","status-publish","format-standard","hentry","category-2644-93-1","category-pyrazoles-derivatives","tag-m-w100-200"],"yoast_head":"\nIntroduction of a new synthetic route about<\/title>\n<meta name=\"description\" content=\"These common heterocyclic compound, 2644-93-1, name is 1,3,5-Trimethyl-1H-pyrazole-4-carbaldehyde, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: pyrazoles-derivatives\" \/>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.pyrazoles-derivatives.com\/?p=5110\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Introduction of a new synthetic route about\" \/>\n<meta property=\"og:description\" content=\"These common heterocyclic compound, 2644-93-1, name is 1,3,5-Trimethyl-1H-pyrazole-4-carbaldehyde, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: pyrazoles-derivatives\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.pyrazoles-derivatives.com\/?p=5110\" \/>\n<meta property=\"og:site_name\" content=\"pyrazoles-derivatives\" \/>\n<meta property=\"article:published_time\" content=\"2021-07-01T19:51:13+00:00\" \/>\n<meta name=\"author\" content=\"Jessica.F\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"Jessica.F\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"2 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\/\/schema.org\",\"@graph\":[{\"@type\":\"WebPage\",\"@id\":\"https:\/\/www.pyrazoles-derivatives.com\/?p=5110\",\"url\":\"https:\/\/www.pyrazoles-derivatives.com\/?p=5110\",\"name\":\"Introduction of a new synthetic route about\",\"isPartOf\":{\"@id\":\"https:\/\/www.pyrazoles-derivatives.com\/#website\"},\"datePublished\":\"2021-07-01T19:51:13+00:00\",\"author\":{\"@id\":\"https:\/\/www.pyrazoles-derivatives.com\/#\/schema\/person\/d9a9f27bed675392c6f363a01ffd49f1\"},\"description\":\"These common heterocyclic compound, 2644-93-1, name is 1,3,5-Trimethyl-1H-pyrazole-4-carbaldehyde, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: pyrazoles-derivatives\",\"breadcrumb\":{\"@id\":\"https:\/\/www.pyrazoles-derivatives.com\/?p=5110#breadcrumb\"},\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"ReadAction\",\"target\":[\"https:\/\/www.pyrazoles-derivatives.com\/?p=5110\"]}]},{\"@type\":\"BreadcrumbList\",\"@id\":\"https:\/\/www.pyrazoles-derivatives.com\/?p=5110#breadcrumb\",\"itemListElement\":[{\"@type\":\"ListItem\",\"position\":1,\"name\":\"\u9996\u9875\",\"item\":\"https:\/\/www.pyrazoles-derivatives.com\/\"},{\"@type\":\"ListItem\",\"position\":2,\"name\":\"Introduction of a new synthetic route about C7H10N2O\"}]},{\"@type\":\"WebSite\",\"@id\":\"https:\/\/www.pyrazoles-derivatives.com\/#website\",\"url\":\"https:\/\/www.pyrazoles-derivatives.com\/\",\"name\":\"pyrazoles-derivatives\",\"description\":\"Several pyrazole derivatives possess important pharmacological activities and they have been proved useful materials in drug research. 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