1. Single Step12%OverviewSteps/Stages Notes1.1R:AlCl3, rt; 100°C1.2R:Br2, 1 h, 100°C; 0.5 h, 100°C; cooledregioselective, Reactants: 1, Reagents: 2,Steps: 1, Stages: 2, Most stages in any onestep: 2ReferencesPreparation of substituted 1-heterocyclylsulfonyl-2-aminomethyl-5-(hetero)aryl-1H-pyrrole derivatives as acidsecretion inhibitors for treating ulcer andrelated disordersBy Kajino, Masahiro et alFrom PCT Int. Appl., 2007026916, 08 Mar2007Experimental ProcedureReference Example 182 3-bromo-2-methylpyridine 2-Methylpyridine (46.6 g) was added dropwise toaluminum chloride (200 g) and the mixture was stirred at 100°C. To a mixture was added dropwisebromine (40.0 g) at the same temperature over 1 hr, and the mixture was further stirred for 30 min.After cooling, the reaction mixture was poured into ice water, concentrated hydrochloric acid wasadded until the mixture was acidified. The obtained solution was washed with ethyl acetate, and theaqueous layer was basified with a 8 mol/L aqueous sodium hydroxide solution. After extraction withdiethyl ether, the extract was washed with saturated brine, dried over anhydrous sodium sulfate, andconcentrated under reduced pressure. The residue was purified by silica gel column chromatography(eluent: hexane-diethyl ether=10:1) to give the title compound as a colorless oil (yield 5.09 g, 12%).1H-NMR (CDCl3)δ : 2.67 (3H, s), 6.98-7.03 (1H, m), 7.78-7.82 (1H, m), 8.40-8.44 (1H, m). CASREACT ®: Copyright © 2013 American Chemical Society. All Rights Reserved. CASREACT contains reactions from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006 John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced under license. All Rights Reserved.2. Single StepOverviewSteps/Stages Notes1.1R:Br2, R:AlCl3, 100°C; 19 h, 100°C Reactants: 1, Reagents: 2, Steps: 1, Stages:1, Most stages in any one step: 1ReferencesSynthesis of C-14 and C-13, H-2-labeled IKKinhibitor: [14C] and [13C4,D3]-N-(6-chloro-7-methoxy-9H-pyrido[3,4-b]indol-8-yl)-2-methyl-3-pyridinecarboxamideBy Li, Yuexian et alFrom Journal of Labelled Compounds andRadiopharmaceuticals, 49(9), 789-799; 2006 CASREACT ®: Copyright © 2013 American Chemical Society. All Rights Reserved. CASREACT contains reactions from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006 John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced under license. All Rights Reserved.3. Single StepOverviewSteps/Stages Notes1.1 -literature preparation, Reactants: 1, Steps: 1,Stages: 1, Most stages in any one step: 1ReferencesThe expedient access to bromo-pyridinecarbaldehyde scaffolds using gem-dibromomethyl intermediatesBy Mandal, Ashis Baran et alFrom Tetrahedron Letters, 46(36), 6033-6036; 2005CASREACT ®: Copyright © 2013 American Chemical Society. All Rights Reserved. CASREACT contains reactions from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006 John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced under license. All Rights Reserved.4. Single StepOverviewSteps/Stages Notes1.1R:AlCl3, R:Br2 1.2R:HCl1.3R:NaHSO3Reactants: 1, Reagents: 4, Steps: 1, Stages: 3, Most stages in any one step: 3ReferencesStructure-activity relationships in the 2-arylcarbapenem series. Synthesis of 1-methyl-2-arylcarbapenemsBy Guthikonda, Ravindra Nath et alFrom Journal of Medicinal Chemistry, 30(5), 871-80; 1987CASREACT ®: Copyright © 2013 American Chemical Society. All Rights Reserved. CASREACT contains reactions from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006 John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced under license. All Rights Reserved.5. Single StepOverviewSteps/Stages Notes1.1R:H2SO4 •SO3, R:Br2Reactants: 1, Reagents: 2, Steps: 1, Stages:1, Most stages in any one step: 1ReferencesSynthesis of tritium labeled thiacoccid and itspharmacokineticsBy Shestakov, A. D. et alFrom Khimiko-Farmatsevticheskii Zhurnal,19(4), 400-5; 1985CASREACT ®: Copyright © 2013 American Chemical Society. All Rights Reserved. CASREACT contains reactions from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006 John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced under license. All Rights Reserved.6. Single Step80%OverviewSteps/Stages Notes1.1R:KBr, R:HBr Reactants: 1, Reagents: 2, Steps: 1, Stages:1, Most stages in any one step: 1ReferencesProduction of 3-chloro- and 3-bromopicolinesBy Talik, Tadeusz et alFrom Prace Naukowe AkademiiEkonomicznej imienia Oskara Langego weWroclawiu, 167, 191-5; 1980CASREACT ®: Copyright © 2013 American Chemical Society. All Rights Reserved. CASREACT contains reactions from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006 John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced under license. All Rights Reserved.。