Cesium carbonate → HCID 86608821, compound

Participants

Reaction Steps

N-{(1R)-1-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl}-1-[(trifluoroacetyl)amino]cyclopropanecarboxamide (1.50 g, 3.377 mmol), 2-bromo-6-flouroaniline (401 ul, 3.545 mmol), tris(dibenzylideneacetone)dipalladium (309 mg, 0.338 mmol), cesium carbonate (1.10 g, 3.377 mmol) and 1.65M tri-t-butylphosphine in dioxane (491 ul, 0.810 mmol) were suspended in dioxane (15 ml), degassed with Argon purge and heated to 90 C for 15 minutes. After this time, the mixture was filtered through a Gelman Acrodisc and the filter was washed with EtOAc (10 ml) and methanol (20 ml). The combined filtrates were concentrated in vacuo and the residue purified by column chromatography eluting with a 0-100% EtAOc/CH2Cl2 gradient to give N-[(1R)-1-(2′-amino-3,3′-difluoro-1,1′-biphenyl-4-yl)ethyl]-1-[(trifluoroacetyl)amino]cyclopropanecarboxamide. Low resolution mass spectrometry: (M+H+)=428.2. 1H NMR (400 MHz, (CD3)2SO) δ 9.79 (s, 1H), 8.28 (d, 1H, J=7.6 Hz), 7.48 (t, 1H, J=8.2 Hz), 7.19-7.26 (m, 2H), 7.02-7.09 (m, 1H), 6.89 (d, 1H, J=7.6 Hz), 6.61-6.68 (m, 1H), 5.22-5.29 (m, 1H), 1.45-1.57 (m, 2H), 1.42 (d, 3H, J=7.1 Hz) and 0.93-1.08 (m, 2H) ppm.

Provenance & Evidence