Multi-step reaction with 10 steps
1.1: 91 percent / KF; HCl; water / methanol / 2 h / Heating
2.1: 75 percent / Red-Al / toluene / 3 h / Heating
3.1: H2SO4; NaNO2 / H2O / 0.08 h
3.2: 77 percent / CuSO4*5H2O; Cu2O / H2O / 0.75 h
4.1: 84 percent / iron; bromine / CH2Cl2 / 20 °C
5.1: 51 percent / 2,6-pyridinedicarboxylic acid; ammonium cerium(VI) nitrate / acetonitrile; H2O
6.1: 59 percent / BF3*OEt2; silver oxide / CH2Cl2 / 2 h / -80 - -20 °C
7.1: 0.26 g / Na2S2O4; NaOH; water / diethyl ether
8.1: 0.30 g / NaH / tetrahydrofuran / 3.5 h
9.1: butyllithium / diethyl ether; hexane / 0.17 h / -70 °C
9.2: 0.29 g / H2O
10.1: 0.15 g / 2,6-pyridinedicarboxylic acid; ammonium cerium(VI) nitrate / H2O; acetonitrile
With
hydrogenchloride; potassium fluoride; sodium hydroxide; n-butyllithium; sodium dithionite; Pyridine-2,6-dicarboxylic acid; ammonium cerium(VI) nitrate; sulfuric acid; boron trifluoride diethyl etherate; water; bromine; iron; sodium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; silver(l) oxide; sodium nitrite;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile;
DOI:10.1002/1099-0690(200207)2002:13<2094::AID-EJOC2094>3.0.CO;2-E