Reference of 945557-04-0, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.945557-04-0, name is 5-Bromo-3-chloropicolinonitrile, molecular formula is C6H2BrClN2, molecular weight is 217.4505, as common compound, the synthetic route is as follows.
Acetyl 2,4,6-tri-O-acetyl-3 -azido-3 -deoxy- 1 -thio-cL-D-galactopyranoside (250 mg, 0.64 mmol) and 5-bromo-3-chloro-pyridine-2-carbonitrile (280 mg, 1.28 mmol) were dissolved in DMF (10 mL). Diethylamine (0.15 ml) was added. The reaction was stirred at room temperature with for 20 h. Water (50 mL) and DCM (50 mL) were added. The aqueous phase was extracted with DCM (50 mL X 2), the combined organic phases were washed with water (100 mL) and brine (100 mL), dried over anhydrous sodium sulphate. Removal of solvent gave a residue. The residue was purified by column chromatography (PE/EA=3/1) to obtain the product (130 mg, 38%).5-Chloro-6-cyano-3-pyridyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-cL-D- galactopyranosidein/z calcd for [C18H18CLN5O7S] [M+H]: 484.0; found: 484.0.5-Bromo-2-cyano-3-pyridyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-cL-D- galactopyranosidein/z calcd for [C18H18BrN5O7S] [M+H]: 528.0; found: 528.0. To a mixture of 5-Chloro-6-cyano-3-pyridyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1- thio-cL-D-galactopyranoside and 5 -Bromo-2-cyano-3 -pyridyl 2,4,6-tri-O-acetyl-3 – azido-3-deoxy-1-thio-cL-D-galactopyranoside (130 mg) in CH3CN (5 mL) were added DIEA (0.23 mL), Copper(I)Iodide(15 mg, 0.08 mmol), CsF(82 mg, 0.54 mmol), 2-(4- chloro-3 ,5 -difluoro-phenyl)ethynyl-trimethyl-silane( 132 mg, 0.54 mmo 1). The reaction was stirred at room temperature for 20 h under a N2 atmosphere. Water (10 mL) and DCM (10 mL) were added. The aqueous phase was extracted with DCM (5 mL X 2), the combined organic phases were washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulphate. Removal of solvent gave a residue. The residue was purified by column chromatography (PE/EA=2/1) to obtain the products 110 (80mg) and 111 (20mg).110) 5-Chloro-6-cyano-3-pyridyl 2,4,6-tri-O-acetyl-3-deoxy-3- [4-(4-chloro-3,5- difluorophenyl)- 1H- 1 ,2,3-triazol- l-ylj – 1-thio-a-D-galactopyranosidem/z calcd for [C26H21Cl2F2N5O7S] [M+H]: 656.0; found: 656.0.1H NMR (400 MHz, CDC13) oe 8.63 (d, J 1.9 Hz, 1H), 8.01 (d, J 2.0 Hz, 1H), 7.83 (s, 1H), 7.45 (t, J= 6.3 Hz, 2H), 6.34 (d, J 5.5 Hz, 1H), 6.16 (dd, J 11.7, 5.6 Hz, 1H), 5.63 (d,J= 2.3 Hz, 1H), 5.20 (dd,J= 11.7, 3.1 Hz, 1H), 4.78 -4.71 (m, 1H), 4.14 (tdd, J= 12.8, 8.7, 4.4 Hz, 3H), 2.08 (s, 3H), 2.00 (s, 3H), 1.98 (s, 3H).ill) 5-Bromo-2-cyano-3-pyridyl 2,4,6-tri-O-acetyl-3-deoxy-3- [4-(4-chloro-3,5- difluorophenyl)- 1H- 1 ,2,3-triazol- l-ylj – 1-thio-cL-D-galactopyranosidem/z calcd for [C26H2iBrCIF2N5O7S] [M+H]: 700.0; found: 700.0.
Statistics shows that 945557-04-0 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-3-chloropicolinonitrile.
Reference:
Patent; GALECTO BIOTECH AB; ZETTERBERG, Fredrik; NILSSON, Ulf; LEFFLER, Hakon; (105 pag.)WO2018/11094; (2018); A1;,
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