Nitrogen → HCID 117804464, compound

Participants

Reaction Conditions

Reaction Steps

To a re-sealable vial was added K2CO3 (206 mg, 1.488 mmol), PdCl2(dppf)-CH2Cl2 adduct (60.8 mg, 0.074 mmol), and the vial was sealed. This vial was evacuated/backfilled with N2 (3×) before addition of (R or S)-methyl 2-methyl-1-(1-(tetrahydro-2H-pyran-4-yl)ethyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-3-carboxylate (318 mg, 0.744 mmol) dissolved in 1,4-dioxane (4 mL), 3-bromopyridine (71.7 μl, 0.744 mmol), and water (400 μL). The reaction was evacuated/backfilled with N2 (3×) before heating to 100° C. The solution was cooled to room temperature and diluted with EtOAc. The solution was filtered and concentrated in vacuo. The crude residue was purified via silica gel chromatography (10 g, EtOAc/hex (1:1)) to afford the title compound (101 mg, 0.267 mmol, 35.9% yield). LCMS 379 (M+1)+.

Provenance & Evidence