Pyridine → N-(4-tert-butylphenyl)-4-{3-[(dimethylamino)sulfonyl]-2-pyridinyl}benzamide

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Reaction Steps

The product from Example 44B (0.917 g, 2.99 mmol) and DMF (0.03 mL) were combined in CH2Cl2 (9 mL) and treated with (COCl)2 (0.32 mL, 3.7 mL). After stirring for 90 minutes, the mixture was diluted with toluene (2 mL) and concentrated to dryness. The residue was dissolved in CH2Cl2 (9 mL) and treated with pyridine (0.36 mL, 4.5 mmol), DMAP (catalytic amount), and 4-tert-butylaniline (0.57 mL, 3.6 mmol). After stirring for 1 hour, the mixture was diluted with water and extracted with CH2Cl2. The organics were dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (75% ethyl acetate in hexanes) to provide the title compound as a solid. 1H NMR (300 MHz, CDCl3)δ 8.84 (dd, 1H), 8.44 (dd, 1H), 7.98 (d, 2H), 7.83 (br s, 1H), 7.72 (d, 2H), 7.58 (d, 2H), 7.51 (dd, 1H), 7.41 (d, 2H), 2.43 (s, 6H), 1.33 (s, 9H); MS (m/z) 438.

Provenance & Evidence