Reference of 745784-04-7 , The common heterocyclic compound, 745784-04-7, name is 3,5-Difluoropicolinic acid, molecular formula is C6H3F2NO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
Intermediate 9: (3,5-difluoro-2-py; 3,5-difluoro-2-pyridinecarboxylic acid (ALFAAESAR , 300 mg, 1.886 mmol) was dissolved in tetrahydrofuran (THF) (10 mL). A/,A/-diethylethanamine (FLUKA, 0.549 mL, 3.96 mmol) was added and mixture was cooled to -10C (ice in acetone). Isobutyl chloroformate (0.269 mL, 2.074 mmol, FLUKA) was added dropwise. Reaction was stirred 20 min at – 10C. Mixture was filtered into a previously prepared solution of sodium borohydride (ALDRICH, 214 mg, 5.66 mmol) in 2 mL of water at 0C and was stirred at 0C for 45 min. HCI (1 N, aq) was added slowly until neutral pH. Aqueous mixture was partitioned with DCM (3x15ml). Organic layer was dried over Na2S04 (anh), filtered and concentrated. Residue was purified by silica gel chromatography using a linear gradient of DCM/MeOH to yield title compound (3,5-difluoro-2-pyridinyl)methanol (1 16 mg, 0.799 mmol, 42.4% yield). 1 H NMR (400 MHz, DMSO-cfe) delta ppm: 8.44-8.45 (s, 1 H), 7.88-7.93 (m, 1 H), 5.35 (t, 1 H), 4.56-4.58 (m, 2H). [ES+MS] m/z 146 (MH+).
The synthetic route of 745784-04-7 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; GLAXO GROUP LIMITED; CASTRO PICHEL, Julia; FERNANDEZ MENENDEZ, Raquel; FERNANDEZ VELANDO, Esther Pilar; GONZALEZ DEL VALLE, Silvia; MALLO-RUBIO, Araceli; WO2012/49161; (2012); A1;,
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