Ammonium formate → HCID 23157422, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-{4-[[3-(tetrahydro-pyran-2-yloxy)-benzyl]-(2,4,6-trimethyl-benzenesulfonyl)-amino]-phenyl}-acrylic acid methyl ester (0.252 g, 0.46 mmol) in methanol was added palladium black (catalytic amount) and ammonium formate (0.289 g, 4.58 mmol). The reaction mixture was stirred at 60° C. for 24 hr. Additional palladium black (catalytic amount) and ammonium formate (0.289 g, 4.58 mmol) were added and the reaction mixture was stirred at 60° C. for 24 hr. The reaction mixture was filtered through diatomaceous earth and the filter cake was washed with water and saturated aqueous sodium bicarbonate. The aqueous solution was washed with methylene chloride. The organic layer was concentrated to afford 0.172 g of the title compound of Step A. 1H NMR (CDCl3) δ 7.10–7.05 (m, 1H), 7.00–6.90 (m, 4H), 6.89–6.80 (m, 4H), 6.75–6.70 (m, 1H), 5.27–5.25 (m, 1H), 4.80–4.70 (m, 2H), 3.85–3.75 (m, 1H), 3.60 (s, 3H), 3.55–3.50 (m, 1H), 2.82 (t, 2H, J=7.6 Hz), 2.53 (t, 2H, J=6.8 Hz), 2.43 (s, 6H), 2.26 (s, 3H), 2.00–1.90 (m, 1H), 1.85–1.75 (m, 2H) 1.65–1.50 (m, 3H).

Provenance & Evidence