6-FLUORO-4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1H-INDAZOLE synthesis
- Product Name:6-FLUORO-4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1H-INDAZOLE
- CAS Number:885698-71-5
- Molecular formula:C13H16BFN2O2
- Molecular Weight:262.09
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Yield:-
Reaction Conditions:
with triethylamine;palladium diacetate;CyJohnPhos in 1,4-dioxane at 80; for 4 h;
Steps:
7
Reference Example 7: 6-Fluoroindazole-4-Boronate Ester (75) To a solution of 4-fluoro-2-nitrotoluene (3.44g) in trifluoroacetic acid (13mL) was added concentrated sulfuric acid (4mL) followed by N-bromosuccinimide (5.92g). The reaction mixture was stirred for 16 h and was then quenched with brine, extracted into ethyl acetate, and dried (MgSO4). The solvent was removed in vacuo to furnish crude l-bromo-5-fluoro-2-methyl-3-nitro-benzene (5.96g). To a solution of crude l-bromo-5-fluoro-2-methyl-3-nitro-benzene (5.96g) inMeOH (9OmL) was added concentrated hydrochloric acid (11.7mL) and iron (6.Ig) and the reaction mixture was heated to reflux. After 16 h, the mixture was cooled, diluted with DCM, washed with sodium carbonate solution, dried (MgSO4) and the solvent removed in vacuo. The residue was purified using flash chromatography to yield 3-bromo-5-fluoro-2-methyl-phenylamine (1.46g).To a solution of 3-bromo-5-fluoro-2-methyl-phenylamine (470mg) in dioxane (6mL) was added triethylamine (1.28mL), palladium acetate (25mg), 2- dicyclohexylphosphino biphenyl (161mg) and pinacol borane (1.001ml) and the mixture was heated to 8O0C for 4 h. The reaction mixture was cooled, diluted with chloroform, washed with brine, dried (MgSO4) and the solvent removed in vacuo. The residue was purified using flash chromatography to yield the desired title compound (466mg).
References:
WO2006/46031,2006,A1 Location in patent:Page/Page column 35
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