N-(3-bromophenyl)cyclohexanecarboxamide

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclohexanecarbonyl chloride (0.74 g, 6.97 mmol) was added to a mixture of 3-bromoaniline (1.0 g, 5.8 mmol), TEA (1.07 mL, 7.55 mmol) and DMAP (cat.) in THF with stirring at 0° C. over 10 min. Stirring was continued for another 30 min and quenched with saturated NaHCO3. The product was extracted with ethyl acetate. Combined organic layers were concentrated under reduced pressure to give a residue which was triturated with pentane to give N-(3-bromophenyl)cyclohexanecarboxamide as an off-white solid. Yield (1.3 g, 79%); 1H NMR (400 MHz, DMSO-d6) δ 9.96 (s, 1H), 7.97 (s, 1H), 7.49 (d, J=8.0 Hz, 1H), 7.26-7.18 (m, 2H), 2.33-2.26 (m, 1H), 1.76 (t, J=14.0 Hz, 4H), 1.65 (d, J=10.4 Hz, 1H), 1.43-1.34 (m, 2H), 1.30-1.12 (m, 3H). Stirring was continued for another 30 min quenched with saturated NaHCO3 The product was extracted with ethyl acetate Combined organic layers were concentrated under reduced pressure to give a residue which was triturated with pentane

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclohexanecarbonyl chloride (0.74 g, 6.97 mmol) was added to a mixture of 3-bromoaniline (1.0 g, 5.8 mmol), TEA (1.07 mL, 7.55 mmol) and DMAP (cat.) in THF with stirring at 0° C. over 10 min. Stirring was continued for another 30 min and quenched with saturated NaHCO3. The product was extracted with ethyl acetate. Combined organic layers were concentrated under reduced pressure to give a residue which was triturated with pentane to give N-(3-bromophenyl)cyclohexanecarboxamide as an off-white solid. Yield (1.3 g, 79%); 1H NMR (400 MHz, DMSO-d6) δ 9.96 (s, 1H), 7.97 (s, 1H), 7.49 (d, J=8.0 Hz, 1H), 7.26-7.18 (m, 2H), 2.33-2.26 (m, 1H), 1.76 (t, J=14.0 Hz, 4H), 1.65 (d, J=10.4 Hz, 1H), 1.43-1.34 (m, 2H), 1.30-1.12 (m, 3H). Stirring was continued for another 30 min quenched with saturated NaHCO3 The product was extracted with ethyl acetate Combined organic layers were concentrated under reduced pressure to give a residue which was triturated with pentane

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclohexanecarbonyl chloride (0.74 g, 6.97 mmol) was added to a mixture of 3-bromoaniline (1.0 g, 5.8 mmol), TEA (1.07 mL, 7.55 mmol) and DMAP (cat.) in THF with stirring at 0° C. over 10 min. Stirring was continued for another 30 min and quenched with saturated NaHCO3. The product was extracted with ethyl acetate. Combined organic layers were concentrated under reduced pressure to give a residue which was triturated with pentane to give N-(3-bromophenyl)cyclohexanecarboxamide as an off-white solid. Yield (1.3 g, 79%); 1H NMR (400 MHz, DMSO-d6) δ 9.96 (s, 1H), 7.97 (s, 1H), 7.49 (d, J=8.0 Hz, 1H), 7.26-7.18 (m, 2H), 2.33-2.26 (m, 1H), 1.76 (t, J=14.0 Hz, 4H), 1.65 (d, J=10.4 Hz, 1H), 1.43-1.34 (m, 2H), 1.30-1.12 (m, 3H). Stirring was continued for another 30 min quenched with saturated NaHCO3 The product was extracted with ethyl acetate Combined organic layers were concentrated under reduced pressure to give a residue which was triturated with pentane