Dichloromethane → HCID 117733756, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of compound 87c (95.0 mg, 0.214 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (48.2 mg, 0.235 mmol), Cs2CO3 (174 mg, 0.534 mmol), and Pd(dppf)2.CH2Cl2 (17.5 mg, 0.0214 mmol) in 1,4-dioxane (3 mL) was added 1.5 mL of water. The resulting mixture was stirred at 90° C. for 4 h. After cooling to rt, the mixture was treated with EtOAc (30 mL) and washed with H2O (2×10 mL) and brine (10 mL). Removal of the solvent gave a residue, which was purified by flash column chromatography on silica gel (0-6% MeOH/DCM) to give compound 87d as a bright yellow-green solid. 1H-NMR (CDCl3; 400 MHz) δ 8.84 (br. s., 2H), 8.65 (d, J=4.9 Hz, 2H), 8.51 (s, 1H), 7.97 (s, 1H), 7.87 (s, 1H), 7.82 (d, J=8.8 Hz, 1H), 6.82 (d, J=8.8 Hz, 1H), 4.96 (s, 2H), 3.66-3.75 (m, 4H), 3.55-3.66 (m, 4H), 3.00 (br. s., 1H), 1.51 (s, 9H). Mass spectrum (LCMS, ESI pos.): Calcd. for C26H29N2O3, 488.2 (M+H). found 488.2.

Provenance & Evidence