Trifluoroacetic acid → HCID 78079921, compound

Participants

Reaction Steps

4-bromo-1-((3-neopentyl-2-oxo-1-oxa-3-azaspiro[4.5]decan-7-yl)methyl)-1H-benzo[d]imidazole-6-carbonitrile (0.100 g, 0.218 mmol) was dissolved in THF (1.00 mL) and treated with tetrakis(triphenylphosphine)palladium(0) (0.503 g, 0.044 mmol) followed by dimethylzinc (1.09 mL, 2.18 mmol). Addition of the dimethylzinc resulted in an exotherm with gas evolution and a color change from brownish-yellow to bright yellow. The reaction mixture was purged with nitrogen and capped. The reaction was allowed to stir at rt for 18 h. The reaction mixture turned dark brown over the course of the reaction. The reaction was quenched with sat. aq. ammonium chloride solution and diluted with EtOAc. The layers were separated, and the organics were washed with brine, dried over MgSO4, filtered, and concentrated. The crude product was purified by reverse-phase HPLC (Sunfire Prep C18 column (30×150 mm); 15 min run; 50 mL/min elution; Solvent A: MeCN/0.1% TFA, Solvent B: water/0.1% TFA, gradient: 35-69% solvent A) to afford the title compound (0.035 g, 31% yield) as the TFA salt. 1H NMR (400 MHz, DMSO-d6) δ 8.55 (br. s., 1H), 8.19 (s, 1H), 7.44 (s, 1H), 4.21 (d, J=7.03 Hz, 2H), 3.31 (dd, J=8.78, 18.57 Hz, 2H), 2.85 (s, 2H), 2.56 (s, 3H), 2.06-2.21 (m, 1H), 1.81 (d, J=11.04 Hz, 1H), 1.73 (d, J=13.80 Hz, 1H), 1.40-1.58 (m, 4H), 1.25-1.35 (m, 1H), 0.95-1.08 (m, 1H), 0.83 (s, 9H). MS (m/z) 395.2 (M+H+).

Provenance & Evidence