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Reagents and conditions: (a) 2-ethyloxirane, cesium carbonate, DMF, 120 °C, 1 h; (b) sodium dithionite, ethanol/DMSO, rt to 90 °C; (c) 2,4-dichloropyridine-3-carbonitrile, DIPEA, DMA, 120 °C, 30–45 min; (d) (2R)- or (2S)-ethyloxirane, cesium carbonate, DMF, 120 °C, 1 h, then 140 °C, 1 h; (e) alkyl bromide or tosylate, cesium carbonate, DMF, 60 °C, 3 days or 120–140 °C, 1 h.
