Multi-step reaction with 7 steps
1.1: 2.47 g / aq. NaOH / ethanol / 1 h / Heating
2.1: thionyl chloride / 2 h / Heating
3.1: 10.9 g / aq. ammonia / acetone / 10 °C
4.1: 9.0 g / cyanuric chloride / dimethylformamide / 0.5 h
5.1: LDA / heptane; tetrahydrofuran; ethylbenzene / 0.33 h / -78 °C
5.2: 750 mg / iodine / heptane; tetrahydrofuran; ethylbenzene / 5 h / -78 °C
6.1: NaH / tetrahydrofuran / 1 h / Heating
6.2: 240 mg / tetrahydrofuran / Heating
7.1: 96 mg / (PPh3)4Pd; aq. NaHCO3 / 1,2-dimethoxy-ethane / 5 h / Heating
With
ammonium hydroxide; sodium hydroxide; tetrakis(triphenylphosphine) palladium(0); thionyl chloride; 1,3,5-trichloro-2,4,6-triazine; sodium hydride; sodium hydrogencarbonate; lithium diisopropyl amide;
In
tetrahydrofuran; 1,2-dimethoxyethane; ethanol; n-heptane; ethylbenzene; N,N-dimethyl-formamide; acetone;
7.1: Suzuki reaction;
DOI:10.1021/jm049237m