Multi-step reaction with 10 steps
1.1: 95 percent / aq. NaOH; n-Bu4NHSO4 / toluene / 3.5 h / 0 - 20 °C
2.1: aq. HF / acetonitrile / 24 h / 20 °C
2.2: 99 percent / TEMPO; NaClO2; NaOCl / aq. phosphate buffer; acetonitrile / 18 h / pH 6.7 / Heating
3.1: 55 percent / 1-hydroxybenzotriazole; EDC; N-methylmorpholine / CH2Cl2 / 16 h / 20 °C
4.1: diethylaminosulfurtrifluoride / CH2Cl2 / 1 h / -78 °C
4.2: K2CO3 / CH2Cl2 / 0.67 h / -78 - 0 °C
4.3: 106.3 mg / BrCCl3; DBU / CH2Cl2 / 20 h / 4 °C
5.1: 54 percent / AgNO3; N-bromosuccinimide / acetone / 1 h / 20 °C
6.1: PdCl2(PPh3)2; n-Bu4SnH / tetrahydrofuran / 3.5 h / -78 - 0 °C
6.2: 92 percent / I2 / tetrahydrofuran
7.1: 94 percent / PdCl2(PPh3)2; CuI; Et3N / acetonitrile / cooling
8.1: 80 percent / DMAP; dicyclohexylcarbodiimide / CH2Cl2 / 14 h / 20 °C
9.1: 94 percent / PdCl2(PPh3)2; CuI / acetonitrile / 1.25 h
10.1: 98 percent / aq. LiOH / tetrahydrofuran / 13.5 h / 20 °C
With
4-methyl-morpholine; dmap; bis-triphenylphosphine-palladium(II) chloride; lithium hydroxide; sodium hydroxide; N-Bromosuccinimide; copper(l) iodide; diethylamino-sulfur trifluoride; n-Bu4SnH; hydrogen fluoride; tetra(n-butyl)ammonium hydrogensulfate; benzotriazol-1-ol; silver nitrate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; dicyclohexyl-carbodiimide;
In
tetrahydrofuran; dichloromethane; acetone; toluene; acetonitrile;
7.1: Sonogashira cross-coupling / 8.1: Sonogashira coupling;
DOI:10.1021/ja0443068