3-溴-2-甲基吡啶的合成方法 Reaction_08_22_2013_153136

1. Single Step

12%

Overview

Steps/Stages Notes

1.1R:AlCl3, rt; 100°C

1.2R:Br2, 1 h, 100°C; 0.5 h, 100°C; cooled

regioselective, Reactants: 1, Reagents: 2,

Steps: 1, Stages: 2, Most stages in any one

step: 2

References

Preparation of substituted 1-

heterocyclylsulfonyl-2-aminomethyl-5-

(hetero)aryl-1H-pyrrole derivatives as acid

secretion inhibitors for treating ulcer and

related disorders

By Kajino, Masahiro et al

From PCT Int. Appl., 2007026916, 08 Mar

2007

Experimental Procedure

Reference Example 182 3-bromo-2-methylpyridine 2-Methylpyridine (46.6 g) was added dropwise to

aluminum chloride (200 g) and the mixture was stirred at 100°C. To a mixture was added dropwise

bromine (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 was

added until the mixture was acidified. The obtained solution was washed with ethyl acetate, and the

aqueous layer was basified with a 8 mol/L aqueous sodium hydroxide solution. After extraction with

diethyl ether, the extract was washed with saturated brine, dried over anhydrous sodium sulfate, and

concentrated 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 Step

Overview

Steps/Stages Notes

1.1R:Br2, R:AlCl3, 100°C; 19 h, 100°C Reactants: 1, Reagents: 2, Steps: 1, Stages:

1, Most stages in any one step: 1

References

Synthesis of C-14 and C-13, H-2-labeled IKK

inhibitor: [14C] and [13C4,D3]-N-(6-chloro-7-

methoxy-9H-pyrido[3,4-b]indol-8-yl)-2-methyl-

3-pyridinecarboxamide

By Li, Yuexian et al

From Journal of Labelled Compounds and

Radiopharmaceuticals, 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 Step

Overview

Steps/Stages Notes

1.1 -literature preparation, Reactants: 1, Steps: 1,

Stages: 1, Most stages in any one step: 1

References

The expedient access to bromo-pyridine

carbaldehyde scaffolds using gem-

dibromomethyl intermediates

By Mandal, Ashis Baran et al

From Tetrahedron Letters, 46(36), 6033-

6036; 2005

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.

4. Single Step

Overview

Steps/Stages Notes