Diisopropylamine → HCID 178432477, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 2 (76 mg, 0.195 mmol) and 4 (62 mg, 0.205 mmol, 1.05 eq) in THF (5 mL) at −78° C. was added freshly prepared 1M LDA dropwise (Prepared from Diisopropylamine and 2.5M n-Butyl Lithium in Hexanes). Upon addition of LDA, an orange color formed and stayed throughout the reaction. After 1.5 hr of stirring at −78° C. the reaction was quenched with 50% aqueous Acetic Acid (5 mL) and the reaction mixture warmed to room temperature. The reaction mixture was diluted with Ethyl Acetate (50 mL) and neutralized using 28-30% Ammonium Hydroxide (aq) until pH˜9. The aqueous layer was extracted one additional time with Ethyl Acetate and the combined organics washed with brine, dried (Na2SO4), and concentrated to a yellow crystalline solid. The crude mixture was purified using Biotage MPLC system (25S column size, 0-10% Methanol/CH2Cl2 over 70CV), giving title compound as an off white solid (60 mg, 0.100 mmol, 51%). 1H NMR (DMSO-d6, 400 MHz): δ 13.9 (s, 1H), δ 9.44 (s, 1H), δ 8.84-8.82 (d, 1H), δ 8.57 (s, 1H), δ 8.39-8.37 (d, 1H), δ 8.27-8.25 (d, 1H), δ 7.90 (bs, 1H), 7.79-7.64 (m, 3H), 7.50-7.35 (m, 1H), δ 7.30-7.28 (d, 1H), δ 3.70-3.30 (m, 8H), δ 2.46 (s, 3H), δ 1.41 (s, 9H); LRMS (m/z): 601 (M+H), 545

Provenance & Evidence