Reaction Steps
The amine (11.3 mg, 23 μmol) was combined with fluorescein isothiocyanate (10.4 mg, 35 μmol) and DIEA (12 μL, 69 μmol) in DMF (400 μL). The solution was stirred 1.5 h and concentrated. The product was purified using HPLC (gradient 50-70% ACN/H2O) to yield 11 as an orange solid (16.2 mg, 18.5 μmol) in 80% yield. 1H (300 MHz, CD3OD): δ 8.11 (s, 1H), 7.70 (d, 1H, J=8.1 Hz), 7.51 (d, 2H, J=7.8 Hz), 7.20 (s, 4H), 7.15 (d, 2H, J=8.5 Hz), 7.08 (d, 1H, J=8.2 Hz), 6.71 (d, 2H, J=8.5 Hz), 6.68 (d, 2H, J=2.1 Hz), 6.54 (dd, 2H, J=8.8, 2.4 Hz), 4.66 (dd, 1H, J=8.4, 5.0 Hz), 3.53 (m, 2H), 3.30 (dd, 1H, J=14.4, 5.0 Hz), 3.05 (dd, 1H, J=14.0, 8.2 Hz), 2.56 (t, 2H, J=7.8 Hz), 1.60-1.57 (m, 4H), 1.31 (br s, 8H); 13C (75 mHz, CD3OD): δ 182.5, 173.4, 170.4, 170.1, 154.6, 136.5, 133.6, 131.8, 130.5, 129.6, 129.3, 126.9, 126.0, 114.1, 144.0, 103.2, 60.4, 60.3, 37.7, 36.3, 32.1, 30.1, 30.0, 29.8, 29.6, 27.6; LC/MS (ESI) (m/z) [M+H]+ calcd 875.3. found 875.3.
