3-BROMO-5-CYCLOPROPYLPYRIDINE

General procedure: Cesium carbonate (165 mg), 1-(tert-butoxycarbonyl)-1H-pyrrol-2-ylboronic acid (136 mg) and Pd(PPh3)4 (24 mg) were added to a 1, 4-dioxane (4 ml) solution containing 3, 5-dibromopyridine (100 mg), followed by reflux for 4 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added. The organic layer was collected, washed with saturated saline, and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (silica gel: silica gel 60 (spherical shape) (Kanto Chemical Co., Inc.); hexane : ethyl acetate = 4:1), and a white solid of tert-butyl 2-(5-bromopyridin-3-yl)-1H-pyrrol-1-carboxylate (73 mg) was thus obtained. 1H-NMR (DMSO-d6, 400MHz) delta:8.64 (d, 1H, J = 2.4Hz), 8.57 (d, 1H, J = 1.9Hz), 8.14-8.12 (m, 1H), 7.47-7.44 (m, 1H), 6.48-6.45 (m, 1H), 6.36-6.33 (m, 1H), 1.35 (s, 9H) MS (ESI, m/z): 323 (M+H), 325 (M+H)Experimental Details: A solution of compound 3 (2.0 g, 10 mmol) and triisopropyl borate (7 mL, 30 mmol) in anhydrous toluene (50 mL) was treated with n-BuLi (12 mL, 30 mmol) at -60 C. under N2 atmosphere. After complete addition, this mixture was stirred at -10 C. for 1 h. The reaction mixture was quenched by adding an aqueous of 2 m HCl, and washed with toluene. The aqueous layer was brought pH=8 by adding Na2CO3, extracted then with ethyl acetate (50 mL×3). The combined organic layers were washed with brine. The solvent was removed under reduced pressure to dryness. The residue was separated by column to give 4.[0553] Experimental Details: A solution of compound 3 (2.0 g, 10 mmol) and triisopropyl borate ( 7 mL, 30 mmol) in anhydrous toluene ( 50 mL) was treated with n-BuLi ( 12 mL, 30 mmol) at -60 C under N2 atmosphere. After complete addition, this mixture was stirred at -10 C for 1 h. The reaction mixture was quenched by adding an aqueous of 2 m HCl, and washed with toluene. The aqueous layer was brought pH = 8 by adding Na2CO3, extracted then with ethyl acetate (50 mL x 3). The combined organic layers were washed with brine. The solvent was removed under reduced pressure to dryness. The residue was separated by column to give 4.[0551] Experimental Details: A mixture of 1 (3.1 g, 13 mmol) and 2 (1 g, 12 mmpl) in an aqueous of 2 M Na2CO3 (15 mL) and toluene (30 mL) was stirred with Pd(PPh3 )4 (0.4 g, 0.029 mmol) under reflux over night. The reaction mixture was extracted with ethyl acetate (100 mL x 3). The combined organic layers were washed with brine. The solvent was removed under reduced pressure to dryness. The residue was separated by column to give 3.Example 28 Experimental Details: A mixture of 1 (3.1 g, 13 mmol) and 2 (1 g, 12 mmpl) in an aqueous of 2 M Na2CO3 (15 mL) and toluene (30 mL) was stirred with Pd(PPh3)4 (0.4 g, 0.029 mmol) under reflux over night. The reaction mixture was extracted with ethyl acetate (100 mL×3). The combined organic layers were washed with brine. The solvent was removed under reduced pressure to dryness. The residue was separated by column to give 3.

Molecular Weight:198.06
XLogP3:2.5
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:196.98401
Monoisotopic Mass:196.98401
Topological Polar Surface Area:12.9
Heavy Atom Count:10
Complexity:122
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes