Nitrogen → HCID 58299668, compound

Participants

Reaction Conditions

Reaction Steps

In a 25 mL single-necked round bottom flask were placed compound 318 (94 mg, 234 μmol, palladium diacetate (21 mg, 93 μmol), and 1,1′-bis(diphenylphosphino)ferrocene (130 mg, 234 μmol). The flask was subjected to 3 cycles of evacuation and back-filling with N2. DMF (3 mL) was added under N2 followed by triethylamine (715 μl, 5140 μmol) and formic acid, 98% (176 μl, 4.67 mmol). The resulting mixture was stirred in an oil bath at 65° C. for 1.5 h. The mixture was poured into ice and saturated NaHCO3 aqueous solution and extracted with 10% i-PrOH/DCM (2×). The combined organics were dried over Na2SO4 and concentrated in vacuo. The residue was subjected to combi-flash column chromatography (methanol/DCM with Et3N) to give compound 319 (48 mg, 80% yield) as an reddish solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.08 (1 H, s), 9.01 (1 H, d, J=5.1 Hz), 8.07 (1 H, d, J=5.1 Hz), 7.28 (2 H, s), 5.42 (1 H, quin, J=8.6 Hz), 2.40-2.49 (2 H, m), 1.92-2.14 (4 H, m), 1.63-1.80 (2 H, m). LCMS-ESI (POS), M/Z, M+1: Found 255.1.

Provenance & Evidence