tert-butyl 5,6-dihydro-4-(4-nitrophenyl)pyridine-1(2H)-carboxylate synthesis
- Product Name:tert-butyl 5,6-dihydro-4-(4-nitrophenyl)pyridine-1(2H)-carboxylate
- CAS Number:387827-33-0
- Molecular formula:C16H20N2O4
- Molecular Weight:304.34
138647-49-1
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Yield:387827-33-0 72%
Reaction Conditions:
Stage #1: 4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzenewith sodium carbonate in Dimethyl ether; for 0.0833333 h;Inert atmosphere;
Stage #2: tetrakis(triphenylphosphine) palladium(0) in Dimethyl ether;water at 80;
Steps:
31.a
Step a) Formation of tert-but -(4-nitrophenyl)-3,6-dihydropyridine-l(2H)-carboxylateA mixture of 4-nitrophenylboronic acid pinacol ester (4.5 g; 18.1 mmol; 1.2 eq.), tert-butyl 4-{[(trifluoromethyl)sulfonyl]oxy}-3,6-dihydropyridine-1 (2H)-carboxylate (5.0 g; 15.1 mmol; 1.0 eq.) and sodium carbonate (1.07 g, 10.1 mmol, 5 eq.) were dissolved in DME (50 ml_) and water (25 ml_). The mixture was degassed for 5min with nitrogen before the addition of Pd(PPh3)4 (349 mg; 0.30 mmol; 0.02 eq.) and heated at 80°C O/N. Water (100 ml_) was added and aqueous phase was extracted with EtOAc (twice). Combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude was purified by flash chromatography on silica (EtOAc:heptane, 10:90) to give the title compound as a yellow solid (3.3g, 72%). 1 H NMR (300 MHz, DMSO-d6) δ 8.24-8.17 (m, 2H), 7.65-7.68 (m, 2H), 6.45 (brs, 1 H), 4.06 (m, 2H), 3.56 (t, 2H), 2.55-2.48 (m, 2H), 1.43 (s, 9H).
References:
WO2012/84704,2012,A1 Location in patent:Page/Page column 132
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