Water → 1,1-dimethylethyl 4-[2-methyl-5-(methyloxy)-4-nitrophenyl]hexahydro-1H-1,4-diazepine-1-carboxylate

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Reaction Conditions

Reaction Steps

To 1-fluoro-2-methyl-5-(methyloxy)-4-nitrobenzene (1.6 g, 8.64 mmol) (Example 113, Step B) in 25 mL of DMSO was added, 1,1-dimethylethyl hexahydro-1H-1,4-diazepine-1-carboxylate (2.6 g, 13 mmol), and K2CO3 (3.6 g, 26 mmol). The mixture was heated to 130° C. for 24 h. The mixture was then poured into 400 mL of H2O and extracted with EtOAc. The product was isolated by flash chromatography to give the title compound of step A (0.7 g, 1.96 mmol, 22%). 1H NMR (400 MHz, DMSO-d6) δ 7.73 (s, 1H), 6.66 (d, J=4.58 Hz, 1H), 3.87 (s, 3H), 3.40-3.52 (m, 4H), 3.33 (d, J=9.34 Hz, 2H), 3.24 (d, J=4.58 Hz, 2H), 2.19 (s, 3H), 1.80-1.90 (m, 2H), 1.36 (s, 5H), 1.30 (s, 4H).

Provenance & Evidence