The origin of a common compound about 2,6-Bis(benzyloxy)-3-bromopyridine

The synthetic route of 16727-47-2 has been constantly updated, and we look forward to future research findings.

Related Products of 16727-47-2 , The common heterocyclic compound, 16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine, molecular formula is C19H16BrNO2, 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.

A mixture of 1-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyridin-2- one 44-3 (200mg, 1.30 mmol), 2,6-bis(benzyloxy)-3-bromopyridine (16-1) (481 mg, 1.30 mmol) and K2CO3 (539 mg, 3.90 mmol) in dioxane / H2O (2ml, 4:1, v/v) was thoroughly degassed under argon followed by addition of Pd2(dba)3 (119 mg, 130 mumol) and tri-tertiarybutylphosphine tetrafluoroborate (75.4 mg, 260 mumol) and finally heating at 100 0C overnight. The reaction mixture was filtered over Celite, the filtrate was concentrated and the crude residue was purified by flash column chromatography to afford 2′,6′-bis(benzyloxy)-1-methyl-[3,3′-bipyridin]-2(1H)-one (44-4) (120 mg, 301 mumol, 23.2 %). LC MS: ES+ 399.2

The synthetic route of 16727-47-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); A1;,
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