2-BROMO-N,N-DIETHYLBENZAMIDE

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Piperazine (489 mg, 4.8 mmol), 2-bromo-N,N-diethyl-benzamide (1 g, 3.95 mmol), Pd2(dba)3 (235 mg, 0.2 mmol), BINAP (442 mg, 0.6 mmol), and cesium carbonate (3 g, 5.53 mmol) were mixed together in toluene (20 mL). The mixture was degassed and heated to 100° C. for about 72 hours. The mixture was diluted with ether (100 mL) and filtered over celite. The filtrate was concentrated and then subjected to chromatography on silica gel to give the title compound (480 mg, 47%) as a brown oil. LRMS (ESI+): 262.2 (M+1) The mixture was degassed The mixture was diluted with ether (100 mL) filtered over celite The filtrate was concentrated

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

Procedure: HOBT (2.72 g, 10.08 mmol), DIPEA (3.52 mL, 20.16 mmol), 2-bromo benzoic acid (4.08 g, 10.08 mmol), and diethyl amine (2.08 mL, 10.08 mmol) were dissolved in DCM (100 mL) and stirred at r.t. for about 30 minutes. EDCI (3.86 g, 10.08 mmol) was added, and the mixture was stirred at r.t. for about 16 hours. The reaction was concentrated to an oil, and the oil was purified via column chromatography to give 2-bromo-N,N-diethyl-benzamide (3.35 g, 68%) as a yellow oil. the mixture was stirred at r.t. for about 16 hours The reaction was concentrated to an oil the oil was purified via column chromatography

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

Procedure: The title compound was prepared using methods analogous to those described in Example 369 using 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-pyrazin-2-amine and 2-bromo-N,N-diethylbenzamide. MS (ESI): mass calcd. for C21H21FN4O, 364.17; m/z found, 365.2 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.59-8.54 (m, 1H), 8.11 (d, J=1.5, 1H), 8.00-7.90 (m, 1H), 7.50-7.36 (m, 5H), 7.36-7.29 (m, 1H), 4.69 (s, 2H), 3.87-3.69 (m, 1H), 3.17-2.92 (m, 2H), 2.85-2.66 (m, 1H), 0.99 (t, J=7.1, 3H), 0.81 (t, J=7.1, 3H).