Methylamine → HCID 20746072, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methylene chloride (2 mL) was added 7-(2-Methyl-1H-indol-5-yloxy)-thieno[3,2-b]pyridine-2-carboxylic acid methyl ester (0.4 g, 1.82 mmol), DBU (0.5 mL, 3.5 mmol), 4-nitrophenyl chloroformate (0.72 g, 3.5 mmol) then stirred at 0° C. for 24 h. Next was added 2.4 mL of methyl amine (2.0 M in THF) via syringe and stirred an addition 1 h. To the reaction mixture was added 50 mL of EtOAc worked-up by portioning between 50/50 NaHCO3 and concentrated. Purification was through silica (30 mL) eluting with EtOAc/CH2Cl2/MeOH (2:1:0.1) combined purified fraction to afford 7-(2-Methyl-1-methylcarbamoyl-1H-indol-5-yloxy)-thieno[3,2-b]pyridine-2-carboxylic acid methyl ester as yellow solid (0.35 g, 74%). HPLC: Rt 3.96 min. (100% area). 1H NMR (CDCl3-d3, 400 MHz) δ: 8.40 (1H, d, J=5.6 Hz), 8.09 (1H, s), 7.64 (1H, d, J=8.8 Hz), 6.92 (1H, dd, J=7.4, 2.2 Hz), 6.84 (1H, d, J=9.1 Hz), 6.49 (1H, d, J=5.3 Hz), 6.23 (1H, s), 5.98 (1H, d, J=4.5 Hz), 3.89 (3H, s), 3.04 (3H, d, 4.5 Hz), 2.52 (3H, s). LCMS (ACPI) M+H+ m/z: 396.2.

Provenance & Evidence