Succinic anhydride → 4-[4-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-indol-1-yl]-4-oxo-butyric acid

Participants

Reaction Conditions

Reaction Steps

To 4-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-1H-indole (37 mg, 0.10 mmol, 1 eq.) was added dimethylformamide (1 mL), triethylamine (0.154 ml, 1.1 mmol, 10 eq.) and succinic anhydride (30 mg, 0.3 mmol, 3 eq.) the reaction was stir at 80° C. for 8 hr and allowed to cool to room temperature. Lithium bis(trimethylsilyl)amide (1 M in THF, 1.2 mL, 1.2 mmol, 12 eq) was added and the reaction was allowed to proceed at room temperature for 24 hr. The reaction was purified by HPLC with a 30-100% acetonitrile in water gradient and dried from dichloromethane/hexanes mixture to yield 4-[4-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-indol-1-yl]-4-oxo-butyric acid as a white solid (16 mg, 34%). LC-MS (ES) calculated for C26H21F2NO5, 465.1; found m/z 466 [M+H]+.

Provenance & Evidence