Ethyl pyridine-4-acetate → HCID 12051089, compound

Participants

Reaction Conditions

Reaction Steps

1-[(1-isocyano-2-(3-methoxyphenyl)ethenyl)sulfonyl]-4-methylbenzene (9.0 g, 0.0285 mol) was dissolved in dry DME (200 mL) and added dropwise to a cooled (0° C.) mixture of ethyl 4-pyridylacetate (9.0 g, 0.545 mol) and potassium t-butoxide (7.1 g, 0.0633 mol) in dry DME (100 mL). After the addition was complete the reaction was warmed to 25° C. and stirred for 3 h. The reaction was then poured into ice water (1200 mL) and extracted into CH2Cl2 (3×500 mL). The combined organics were dried over Na2SO4, filtered and evaporated in vacuo to give a solid. This solid was then triturated with ether and filtered to give 3.0 g of pure 3-(3-methoxyphenyl)-4-(4-pyridyl)pyrrole. The filtrate was again evaporated in vacuo and then triturated with a 50/50 mixture of CH2Cl2 and ether to give an additional 1.5 g of pure product. Finally the filtrate was evaporated in vacuo and purified on SiO2 eluting with ethyl acetate to give another 0.5 g of pure product resulting in a 70% combined yield. 1HNMR (DMSO-d6) δ 11.38 (1H, br s, NH), 8.37 (2H, d, J=6.1), 7.24-7.17 (4H, m), 7.02-7.00 (1H, m), 6.80-6.77 (3H, m), 3.68 (3H, s).

Provenance & Evidence