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1174028-24-0

3-PYRIDINEMETHANOL,6-CHLORO-5-FLUORO synthesis

1synthesis methods
-

Yield:1174028-24-0 41%

Reaction Conditions:

with formic acid;triethylamine;tetrakis(triphenylphosphine) palladium(0) in 1,4-dioxane at 110; for 6 h;

Steps:

5.b

(b) (6-Chloro-5-fluoro-3-pyridinyl)methanolTo a solution of (2,6-dichloro-5-fluoro-3-pyridinyl)methanol (4.4 g, 22.45 mmol) in 1,4-dioxane (20 ml) was added Et3N (3.42 ml, 24.69 mmol), formic acid (0.947 ml, 24.69 mmol) and Pd(PPh3)4 (1.297 g, 1.122 mmol). The mixture was then heated at 110° C. for 6 h in a pressure tube. The crude was diluted with H2O and extracted twice with EtOAc. The combined organic phases were washed with H2O and sat. NaCl, dried over Na2SO4 and concentrated under reduced pressure. The crude was purified by flash chromatography using Flashmaster II, a 70 g spherical silica gel cartridge and DCM/MeOH 98:2 as eluent to give 2.0 g (41%) of the title compound pure enough to be used in the next step.1H-NMR (δ, ppm, CDCl3): 8.18 (d, 1H), 7.70 (dd, 1H), 4.78 (bs, 2H), 1.93 (bs, 1H). [ES MS] m/z 162 (MH+).

References:

US2009/306089,2009,A1 Location in patent:Page/Page column 27