Allyl Alcohol → 3-(1-Oxido-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-yl)-1-propanol

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Reaction Conditions

Reaction Steps

Pd(OAc)2 (18 mg, 0.08 mmol) was added to a degassed solution of iodide 66 (250 mg, 0.80 mmol), allyl alcohol (0.27 mL, 3.40 mmol), tetrabutylammonium chloride (182 mg, 0.80 mmol) and NaHCO3 (147 mg, 1.76 mmol) in acetonitrile (12.5 mL) and the solution irradiated in a Milestone MicroSYNTH reactor for 15 min at 150° C. (max. 400 watt). After cooling, the mixture was quenched with saturated aqueous NH4Cl solution (10 ml) and filtered. The filtrate was extracted with EtOAc (3×20 ml), dried and the solvent evaporated. The crude residue was dissolved in MeOH (20 mL), cooled to −40° C. and NaBH4 (2×40 mg, 2.12 mmol) in MeOH (20 mL) added to it. The solution was stirred at −40° C. for 1, then HOAc (0.1 mL) added, warmed to 20° C. and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (80-100%) EtOAc/pet. ether, to give alcohol 70 (89 mg, 45%) as an off-white solid; spectroscopically identical to the sample prepared above.

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