Water → HCID 10225015, compound

Participants

Reaction Steps

Boc-indole 2-3 (120 mg, 0.22 mmol) was slurried in 3 mL of CH2Cl2, H2O (10 μL) and dimethylsulfide (10 μL). TFA (3 mL) was added and the reaction was observed to become homogenous. The reaction was then stirred for 1.5 hours. The excess TFA/CH2Cl2 was removed under reduced pressure. The residue was dissolved in DMSO and purified via reverse phase HPLC (95%-5% H2O/AcCN). The pure fractions were combined in a separatory funnel and the pH adjusted to 11 by the addition of 0.5N NaOH. The mixture was then extracted with CH2Cl2/nBuOH (3:1, 2×100 mL). The organic layer was washed with brine, dried with Na2SO4 and concentrated to give 2-4 as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 11.43 (s, 1H), 8.52 (s, 1H), 7.73 (d, 1H, J=7.8 Hz), 7.51 (d, 2H, J=7.3 Hz), 7.44 (bs, 1H), 7.37 (d, 1H, J=8.1 Hz), 7.31 (bs, 1H), 7.24 (t, 1H, J=7.3 Hz), 6.98 (d, 1H, J=7.6 Hz), 3.62 (s, 2H), 3.12 (m, 4H), 2.87 (s, 3H), 2.48 (m, 4H).

Provenance & Evidence