Triphenylphosphine → 5-(5-Hydroxymethyl-2-pyridin-4-yl-furan-3-yl)indan-1-one

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Reaction Steps

The product from Step 2 (737 mg, 2.9 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)indanone (0.25 g, 1 mmol) (WO98/45265) (750 mg, 2.9 mmol), potassium acetate (854 mg, 8.7 mmol), triphenylphosphine (79 mg, 0.3 mmol) and palladium (II) acetate (34 mg, 0.15 mmol) were heated at 95° C. in 1:1:1 ethanol:water:N,N-dimethylformamide (10 ml) for 16 hours. After cooling the solution was partitioned between ethylacetate/water and the aqueous phase extracted with ethylacetate (×3). The combined organic extracts were washed with water (×3), brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with ethylacetate to afford the title product (383 mg, 43%); MS(ES+) m/e 306 [M+H]+.

Provenance & Evidence