Dimethyl Sulfide → HCID 58882981, compound

Participants

Reaction Steps

A solution of 1M BH3.SMe2 in CH2Cl2 (7 mL, 7 mmol) was added dropwise to a solution of ethyl 3-amino-5-benzylpyridine-2-carboxylate (600 mg, 2.34 mmol) and 4-methylsulfonyl benzaldehyde (647 mg, 3.51 mmol) in CH2Cl2 (8 mL) and HOAc (4 mL). The mixture was stirred at rt for 30 min and additional amounts of 1M BH3.SMe2 (2 mL, 2 mmol) and 4-methylsulfonyl benzaldehyde (160 mg, 3.51 mmol) were added. After stirring overnight at rt, the solution was concentrated in vacuo, dissolved in CH2Cl2 and washed with NaHCO3 solution. The organic layer was dried, concentrated and chromatographed on silica gel eluting with 0-5% MeOH/CH2Cl2. This afforded the product as an amber foam: 1H NMR (CDCl3) δ 8.31 (1H, br m), 7.97 (1H, s), 7.86 (2H, d, J=8 Hz), 7.42 (2H, d, J=8 Hz), 7.22 (3H, m), 7.02 (2H, dd, J=8, 2 Hz), 6.58 (1H, s), 4.46 (2H, br), 4.46 (2H, q, J=7 Hz), 3.87 (2H, s), 3.04 (3H, s), 1.45 (3H, t, J=7 Hz); HRMS calcd for C23H24N2O4S+H+: 425.1535. Found: 425.1524.

Provenance & Evidence