Potassium Phosphate, Tribasic → 4-[(phenylmethyl)oxy]-1-{4-[(phenylmethyl)oxy]phenyl}-1H-indole

Participants

Reaction Conditions

Reaction Steps

4-[(phenylmethyl)oxy]-1H-indole (504 mg, 2.26 mmoL), 4-bromophenyl phenylmethyl ether (580 mg, 1.88 mmoL), K3PO4 (998 mg, 4.7 mmoL) and L-Proline (43.3 mg, 0.376 mmoL) were dissolved in 1,4-Dioxane (4 mL) in a microwave vial and degassed by sonication under a flow of argon. To this was added CuI (18 mg, 0.094 mmoL) and the solution was heated to 100° C. in the microwave reactor. After 5 hours a second portion of CuI (48 mg, 0.252 mmoL) and L-Proline (40 mg, 0.347 mmoL) were added and the mixture heated for 2 more hours. The reaction mixture was filtered through a pad of celite and concentrated. The residue was partitioned between ethyl acetate (100 mL)/water (100 mL), the phases were separated and the aqueous phase re-extracted with ethyl acetate (100 mL). The combined organic phases were washed with brine (2×50 mL) then water (50 mL) and finally dried over MgSO4. The crude product was purified by flash chromatography (Biotage SP4) eluting with a gradient of 0 to 30% Et2O in hexane to give the title compound (D24), (143 mg).

Provenance & Evidence