Trimethylaluminum → HCID 58293433, compound

Participants

Reaction Conditions

Reaction Steps

(R)-1-(2-(6-chloro-3-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)-3-methylbutanoyl)azetidine-3-carbonitrile (30 mg, 0.081 mmol), Pd(Ph3P)4 (47 mg, 0.04 mmol), and dioxane (2 mL) were combined in a 5 mL microwave vial. The mixture was purged with nitrogen, and trimethylaluminum (2.0M/toluene, 0.24 mL, 0.48 mmol) was added. The vial was sealed and the reaction mixture was heated in a Biotage Initiator™ microwave for 1 h at 120° C. The reaction was repeated 4 times at the same scale. The reaction mixtures were combined, and the resulting mixture was quenched with water (0.5 mL), concentrated, and purified by preparative HPLC (10-30% AcCN/H2O with 0.035% TFA) followed by flash chromatography (5% MeOH/95% DCM) to give the title compound as a light yellow solid (41 mg, 29%). 1H NMR (500 MHz, CD3OD) δ 0.92 (d, J=6.8 Hz, 3H), 1.07 (dd, J=15.9, 6.1 Hz, 3H), 2.42 (d, J=6.35 Hz, 3H), 3.69-3.77 (m, 1H), 4.19-4.22 (m, 1H), 4.32-4.34 (m, 1H), 4.53-4.59 (m, 1H), 4.68-4.72 (m, 1H), 5.20-5.33 (m, 3H), 7.98 (d, J=19.5 Hz, 1H), 8.27 (s, 1H). [M+H] calc'd for C19H21N5O2, 352; found, 352.

Provenance & Evidence