Tetrahydrofuran → HCID 10227850, compound

Participants

Reaction Steps

A solution of Example 94A (0.05 g, 0.114 mmol), methoxyethylphosphonium bromide (0.068 g, 0.171 mmol) and aqueous sodium hydroxide (1 mL, 6.0M) in THF (1 mL) was stirred for 16 hours, and then diluted with EtOAc (10 mL) and brine (25 mL). The layers were separated and the organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure. The residue and 10% Pd on carbon (0.005 g) in anhydrous THF (2 mL) were shaken under hydrogen gas (balloon) for 6 hours. The mixture was filtered through diatomaceous earth (Celite®), washing the filtrant with dry TUF (2×20 mL). The combined organics were concentrated under reduced pressure and purified by HPLC using 0.1% TFA and MeCN to provide the titled compound (1H NMR (300 MHz, DMSO-d6) δ 9.84 (s, 1H), 8.33 (d, J=9 Hz, 1H), 7.26-7.22 (m, 2H), 7.15 (t, J=8 Hz, 1H), 6.92-6.80 (m, 4H), 6.73 (d, J=8 Hz, 1H), 6.65 (d, J=9 Hz, 1H), 6.18 (s, 1H), 3.89 (t, J=6 Hz, 2H), 3.88 (s, 3H), 3.46-3.43 (m, 2H), 3.21 (s, 3H), 3.00 (s, 3H), 1.71-1.57 (m, 4H); MS (ESI, −Q1MS) m/e 508 (M−H).

Provenance & Evidence