Trimethyl borate → HCID 59713649, compound

Participants

Reaction Conditions

Reaction Steps

As illustrated in the scheme above, absolution of 2-bromo-6-methoxypyridine (0.022 mL, 0.18 mmol) in dry Et2O (0.3 mL) was added to a solution of n-BuLi (0.12 mL of 1.6 M in hexanes, 0.19 mmol) maintained at −40° C. The reaction was stirred at −40° C. for 20 min., and then B(OMe)3 (0.022 mL, 0.19 mmol) was added dropwise. The reaction was stirred at −40° C. for 30 min., and then at room temperature for 3.5 h. The reaction was concentrated in vacuo, anhydrous MeOH was added to the residue, and the reaction was concentrated in vacuo once again. Dry DME (0.8 mL), 5,7-dichloro-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (0.0392 g, 0.161 mmol), Pd(PPh3)4 (0.0093 g, 0.0080 mmol) and CsF (0.0612 g, 0.403 mmol) were added to the residue, and the mixture was heated to reflux for 15 h. Water (5 mL) and CH2Cl2 (5 mL) were added to the reaction mixture, and the layers were separated. The aqueous phase was extracted with additional CH2Cl2 (3×), and the combined organic phases were dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the crude product by silica gel column chromatography (2:1 CH2Cl2:EtOAc) provided the title compound (0.029 g, 57%). 1H-NMR (CDCl3): δ 7.77 (d, J=7.6 Hz, 1H), 7.71-7.64 (m, 2H), 7.49 (dd, J=2.4 Hz, J=8.8 Hz, 1H), 7.27 (d, J=8.8 Hz, 1H), 6.83 (d, J=8.0 Hz, 1H), 4.85 (d, J=10.8 Hz, 1H), 3.86 (d, J=10.4 Hz, 1H), 3.81 (s, 3H), 3.39 (s, 3H). MS (ESI) (M+H)+=316.

Provenance & Evidence