Potassium Carbonate → 2-Methyl-6-((1-phenylpiperidin-4-yl)methyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

Participants

Reaction Conditions

Reaction Steps

To a 20 mL screw cap vial, under N2, 4-methylene-1-phenylpiperidine (0.0906 g, 0.523 mmol) was diluted with 0.5M THF solution of 9-BBN (1.046 mL, 0.523 mmol) and stirred at 75° C. for 1 hr. The reaction mixture was then added to a suspension of 6-bromo-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one 19 (0.127 g, 0.523 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.0128 g, 0.016 mmol) and K2CO3 (0.145 g, 1.046 mmol) in DMF (1.0 mL) and water (0.1 mL) and stirred at 60° C. for 4 hr. The mixture was cooled to RT, diluted with water (20 mL) and extracted with ethyl acetate (2×20 mL). The combined organic layers was washed with brine, dried with MgSO4, filtered and concentrated in vacuo. Purification by flash column chromatography (10%-50% EA/Hex) provided the desired product as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.21-1.32 (m, 2H) 1.40 (d, J=6.82 Hz, 3H) 1.47 (br. s., 1 H) 1.64 (d, J=13.14 Hz, 2H) 2.45 (d, J=6.82 Hz, 2H) 2.52-2.62 (m, 2H) 3.59-3.70 (m, 2H) 4.55-4.67 (m, 1H) 6.65-6.78 (m, 3H) 6.81-6.94 (m, 3H) 7.11-7.22 (m, 2H) 10.58 (s, 1 H). ESI-MS: m/z 337.3 (M+H)+.

Provenance & Evidence