Ethyl Acetate → HCID 21886609, compound

Participants

Reaction Conditions

Reaction Steps

To a slurry of Rieke Zinc (370 mg, 5.64 mmol) in THF (7.4 mL) was added a solution of 2-bromo-6-dimethoxymethyl-pyridine (400 mg, 1.7 mmol) in THF (2.6 mL). The suspension was heated to 65° C. for 2 h and the solution was filtered through a 0.23 μm syringe filter into a THF solution of {[4-(3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester ((Example 27: step c) (250 mg, 0.5 mmol)) and Pd(PPh3)4 (0.112 mg, 0.1 mmol).The reaction was heated at 80° C. for 30 min, cooled, and was poured into aqueous NaHCO3. EtOAc (70 mL) was added and the layers were separated. The organic layer was washed with NH4Cl (2×20 mL), NaHCO3 (20 mL) and brine (30 mL) and was dried over sodium sulfate. Concentration of the solution followed by SiO2 flash column chromatography of the residue yielded 200 mg of the title compound which was contaminated with 2-dimethoxymethyl-pyridine. The material was treated with 1:1 TFA/DCM as described in Example 1: step d. Analogous purification by C18-HPLC yielded the title compound (118 mg, 38%) as a white solid. 1H-NMR (CD3OD) (aldehyde exists in hydrated form (acetal)) δ 8.60 (m, 2H), 8.44 (s, 1H), 8.33 (d, 1H, J=7.9), 8.27 (d, 1H, J=7.7), 8.23 (d, 1H, J=7.7), 8.12 (d, 1H, J=7.9), 7.9 (t, 1H, J=7.7), 5.82 (s, 1H), 2.74 (s, 3H). ESI-MS (m/z) (sample in MeOH): Calcd. for C18H15N3O3S3 (M+H): 418.0; found: 449.9 (MeOH adduct).

Provenance & Evidence