Diethyl Ether → HCID 68699625, compound

Participants

Reaction Steps

A suspension of [3-(7-bromo-1-cyclohexylmethyl-1H-indol-3-yl)-[1,2,4]thiadiazol-5-yl]-methanol (prepared from 7-bromoindole as described in Example 7; 2×250 mg, 0.16 mmol), zinc (II) cyanide (2×72 mg, 0.61 mmol) and tetrakis(triphenylphosphine)-palladium(0) (2×21 mg, 18.3 μmol) in DMF (2×4 ml) was subjected to microwave irradiation at 200° C. for 5 min using an Emrys™ Optimizer EXP. The reactions were combined and poured into a separating funnel, to this was added dichloromethane (˜50 ml). The organics were washed successively with water (2×20 ml), 1M aqueous HCl (20 ml) and brine (20 ml), dried over magnesium sulfate, filtered, and the solvent removed in vacuo. The resulting oil was purified by flash column chromatography eluting with 50-100% (v/v) dichloromethane in heptane and then diethyl ether to give 1-cyclohexylmethyl-3-(5-hydroxymethyl-[1,2,4]thiadiazol-3-yl)-1H-indole-7-carbonitrile (416 mg, 1.18 mmol) as a light yellow oil which crystallised on standing.

Provenance & Evidence