Isoamylamine → 3-fluoro-N-(3-methyl-butyl)-pyridine-2-carboxylic acid amide

To a solution of 3-fluoro-pyridine-2-carboxylic acid (0.50 g, 3.54 mmol) in dimethylformamide (6 ml) are added O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (3.41 g, 10.63 mmol) and N-methylmorpholine (1.56 ml, 14.2 mmol) at 0° C. followed by the addition of 3-methyl-butyl-amine (0.61 ml, 5.32 mmol). The reaction mixture is stirred at RT for 2 h. After completion of the reaction, the mixture is poured onto ice-water, extracted with EtOAc (3×50 ml). The combined organic layers are washed with brine (50 ml), dried over sodium sulfate and evaporated to dryness to yield the crude product, which is purified by column chromatography (silica gel, 50% EtOAc/hexane) affording 3-fluoro-N-(3-methyl-butyl)-pyridine-2-carboxylic acid amide (0.31 g, 1.47 mmol, 42%).

1. customAfter completion of the reaction
2. additionthe mixture is poured onto ice-water
3. extractionextracted with EtOAc (3×50 ml)
4. washThe combined organic layers are washed with brine (50 ml)
5. dry with materialdried over sodium sulfate
6. customevaporated to dryness
7. customto yield the crude product, which
8. customis purified by column chromatography (silica gel, 50% EtOAc/hexane)

ORD record

ord-cf44d8fa23d74b7c90773d664e611db7

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09284286B2