Diisopropylethylamine → Tert-butyl [2-{[4-(bromomethyl)benzoyl]amino}-4-(2-thienyl)phenyl]carbamate

Participants

Reaction Conditions

Reaction Steps

4-Bromomethyl-benzoyl bromide (0.70 g, 2.52 mmol) was made 0.21 M in anhydrous DCM and cooled to −78° C. To this stirring solution was added (2-amino-4-thiophen-2-yl-phenyl)-carbamic acid tert-butyl ester (0.73 g, 2.52 mmol) followed by DIPEA (0.98 g, 7.56 mmol). The resulting solution was warmed to ambient temperature and stirred for 18 hours. The reaction mixture was then diluted with 0.1 N HCl and extracted with EtOAc. The organic layer was then washed with saturated aqueous sodium bicarbonate, brine, dried (MgSO4), and concentrated in vacuo to afford the title compound: 1H NMR (DMSO-d6, 600 MHz) 9.90 (s, 1H), 8.72 (s, 1H), 7.94 (d, J=7.8. Hz, 2H), 7.78-7.80 (m, 1H), 7.57-7.62 (m, 3H), 7.47-7.51 (m, 2H), 7.42-7.44 (m, 1H), 7.09-7.12 (m, 1H), 4.77 (s, 2H), 1.43 (s, 9H).

Provenance & Evidence