Sodium t-butoxide → HCID 86719505, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-5-trifluoromethyl-benzothiazole (430 mg, 1.4 mmol, 1 eq.) in toluene (15 ml) was added sodium tert-butoxide (546 mg, 5.7 mmol, 4 eq.), BINAP (10 mg, 0.015 mmol, 0.01 eq.) and 2-[4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexyloxy]-1-piperazin-1-yl-ethanone hydrochloride (1.33 g, 2.84 mmol, 2 eq.). The solution was flushed with nitrogen and evacuated three times before adding Pd2(dba)3-CHCl3 (31 mg, 0.03 mmol, 0.02 eq.) and flushing/evacuating a final time. The slurry was heated to for 18 hours at 70° C. before concentrating in vacuo. The residue was applied onto a silica gel column and eluted with Heptanes/EtOAc to afford 2-[4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexyloxy]-1-[4-(5-trifluoromethyl-benzothiazol-2-yl)-piperazin-1-yl]-ethanone as a yellow solid (662 mg, 73.8%). (CI, m/z): [M+H]+ 632; 1H NMR (400 MHz, CDCl3): δ 1.29-1.38 (m, 2H), 1.41-1.56 (m, 2H), 2.16 (d, J=8.9 Hz, 4H), 3.26-3.53 (m, 2H), 3.55-3.90 (m, 8H), 4.26 (s, 2H), 4.47 (d, J=7.6 Hz, 1H), 6.63 (dd, J=9.1, 2.5 Hz, 1H), 6.85 (d, J=2.3 Hz, 1H), 7.36 (d, J=8.2 Hz, 1H), 7.72 (d, J=8.2 Hz, 1H), 7.81 (s, 1H), 8.01 (d, J=9.0 Hz, 1H).

Provenance & Evidence