Fluoride Ion → HCID 44158703, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-benzothiazol-2-yl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-ylamine (BB8) (151 mg, 0.428 mmol), (2R,4S)-4-(4-iodopyrazol-1-yl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (177 mg, 0.389 mmol), Pd(PPh3)4 (20 mg, 0.02 mmol), potass fluoride (67.8 mg, 1.17 mmol), and 4:1 dioxane:water (4 mL) was heated in the microwave reactor at 85° C. for 30 min. The solution was dry-loaded onto silica gel for column chromatography, eluting with 2→5% MeOH/DCM. The fractions containing the product were concentrated in vacuo and dissolved in conc. HCl. The material was heated to 60° C. for 3 h in a sealed tube. The solvent was removed on the corrosive pump to afford the title compound as an orange solid. 1H NMR (400 MHz, CD3OD): δ=2.55-2.67 (m, 1H), 2.74 (br. s., 1H), 3.76-3.87 (m, 2H), 4.45 (t, J=8.6 Hz, 1H), 5.25 (dd, J=6.1, 3.0 Hz, 1H), 7.44 (t, J=7.6 Hz, 1H), 7.49-7.55 (m, 1H), 7.88 (s, 1H), 7.97 (d, J=7.6 Hz, 1H), 8.02 (d, J=7.8 Hz, 1H), 8.06 (s, 1H), 8.16 (d, J=2.0 Hz, 1H), 8.30 (d, J=2.0 Hz, 1H).

Provenance & Evidence