Water → HCID 118353310, compound

Participants

Reaction Conditions

Reaction Steps

To 2-(2-pyridinyl)aniline (S1) (851 mg, 5.00 mmol, 1.00 equiv) in CH2Cl2 (10 mL) at 0 ° C. was added pyridine (1.60 mL, 20.0 mmol, 4.00 equiv) and 2-nitrobenzenesulfonyl chloride (2.20 g, 10.0 mmol, 2.00 equiv). The reaction mixture was warmed to 23 ° C. and stirred for 2.0 hr before the addition of water (10 mL). The phases were separated and the aqueous layer was extracted with CH2Cl2 (3×8 mL). The combined organic phases were washed with brine (30 mL) and dried (Na2SO4). The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica gel eluting with hexanes/EtOAc 3:7 (v/v) to afford 1.33 g of the title compound as a pale-yellow solid (75%). Rf=0.12 (hexanes/EtOAc 7:3 (v/v)). Melting Point: 91-94 ° C. NMR Spectroscopy: 1H NMR (500 MHz, CDCl3, 23 ° C., δ): 8.73 (d, J=5.0 Hz, 1H), 7.94 (dd, J=7.5 Hz, 2.0 Hz, 1H), 7.82 (dd, J=8.0 Hz, 1.0 Hz, 1H), 7.74 (ddd, J=7.5 Hz, 7.5 Hz, 2.0 Hz, 1H), 7.63-7.52 (m, 5H), 7.38 (ddd, J=7.5 Hz, 7.5 Hz, 1.5 Hz, 1H), 7.27-7.24 (m, 1H), 7.18 (ddd, J=7.5 Hz, 7.5 Hz, 1.0 Hz, 1H). 13C NMR (125 MHz, CDCl3, 23 ° C., δ): 156.9, 156.2, 148.0, 137.9, 136.4, 133.6, 132.2, 131.0, 130.0, 129.0, 127.1, 125.0, 124.7, 122.4, 121.9, 121.9, 110.9. Mass Spectrometry: HRMS-FIA (m/z): Calcd for [C17H13N3O4S+H], 356.06995. Found, 356.07008.

Provenance & Evidence