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ChemicalBook CAS DataBase List 2-FLUORO-5-(ISOPROPYLCARBAMOYL)BENZENEBORONIC ACID
874289-49-3

2-FLUORO-5-(ISOPROPYLCARBAMOYL)BENZENEBORONIC ACID synthesis

2synthesis methods
866775-09-9 Synthesis
3-AMINO-6-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER

866775-09-9
74 suppliers
$60.00/100mg

2-Pyridinecarboxylic acid, 3-amino-6-[2-fluoro-5-[[(1-methylethyl)amino]carbonyl]phenyl]-, methyl ester

1052714-98-3
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Yield:1052714-98-3 98%

Reaction Conditions:

with sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 in 1,2-dimethoxyethane;water at 120; for 1.5 h;Suzuki Coupling;

Steps:



Synthesis of methyl 3-amino- -(2-fluoro-5-isopropylcabamoyl)phenyl)-picolinate[00160] A solution of methyl 3-amino-6-bromopicolinate (1.0 equiv.),N-isopropyl 3-borono-4-fluorobenzamide (1.1 equiv.), and Pd(dppf)Cl2-DCM (0.15 equiv.) in DME/2M Na2C03 (3 : 1), at a concentration of 0.5 M, was stirred at 120°C for 1.5 hours. The reaction was filtered and washed with EtOAc. The organic was partitioned with H20 (25mL), washed with NaCl(sat.) (25mL), dried over MgS04, and the volatiles were removed in vacuo. The residue was diluted in EtOAc and passed through a silica gel plug and the volatiles were removed in vacuo yielding methyl 3-amino-6-(2- fluoro-5-isopropylcabamoyl)phenyl)picolinate (60%). LCMS (m/z): 332.2 (MH+); LC R, = 2.9 min.

References:

WO2012/4217,2012,A1 Location in patent:Page/Page column 69-70